Heterocyclic compound and organic light emitting device using same

ABSTRACT

The present application provides a hetero-cyclic compound capable of significantly enhancing lifespan, efficiency, electrochemical stability and thermal stability of an organic light emitting device, and an organic light emitting device containing the hetero-cyclic compound in an organic compound layer.

TECHNICAL FIELD

This application claims priority to and the benefits of Korean PatentApplication No. 10-2016-0085748, filed with the Korean IntellectualProperty Office on Jul. 6, 2016, the entire contents of which areincorporated herein by reference.

The present application relates to a hetero-cyclic compound and anorganic light emitting device using the same.

BACKGROUND ART

An electroluminescent device is one type of self-emissive displaydevices, and has an advantage of having a wide viewing angle, and a highresponse speed as well as having an excellent contrast.

An organic light emitting device has a structure disposing an organicthin film between two electrodes. When a voltage is applied to anorganic light emitting device having such a structure, electrons andholes injected from the two electrodes bind and pair in the organic thinfilm, and light emits as these annihilate. The organic thin film may beformed in a single layer or a multilayer as necessary.

the organic thin film, compounds capable of forming a light emittinglayer themselves may be used alone, or compounds capable of performing arole of a host or a dopant of a host-dopant-based light emitting layermay also be used. In addition thereto, compounds capable of performingroles of hole injection, hole transfer, electron blocking, holeblocking, electron transfer, electron injection and the like may also beused as a material of the organic thin film.

Development of an organic thin film material has been continuouslyrequired for enhancing performance, lifespan or efficiency of an organiclight emitting device.

PRIOR ART DOCUMENTS Patent Documents

U.S. Pat. No. 4,356,429

DISCLOSURE Technical Problem

Researches for an organic light emitting device comprising a compoundcapable of satisfying conditions required for materials usable in anorganic light emitting device, for example, a proper energy level,electrochemical stability, thermal stability and the like, and having achemical structure that may perform various roles required in an organiclight emitting device depending on substituents have been required.

Technical Solution

One embodiment of the present application provides a hetero-cycliccompound represented by the following Chemical Formula 1:

in Chemical Formula 1,

L1 is a direct bond; a substituted or unsubstituted C₆ to C₆₀ arylenegroup; or a C₂ to C₆₀ heteroarylene group,

Z1 is selected from the group consisting of hydrogen; deuterium; ahalogen group; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₆ to C₆₀ aryl group; asubstituted or unsubstituted C₂ to C₆₀ heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with a C₁ toC₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂ to C₆₀ heteroaryl group,

m is an integer of 0 to 4,

n is an integer of 1 to 4,

R1 to R11 are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₂ to C₆₀ alkenyl group; asubstituted or unsubstituted C₂ to C₆₀ alkynyl group; a substituted orunsubstituted C₁ to C₆₀ alkoxy group; a substituted or unsubstituted C₃to C₆₀ cycloalkyl group; a substituted or unsubstituted C₂ to C₆₀heterocycloalkyl group; a substituted or unsubstituted C₆ to C₆₀ arylgroup; a substituted or unsubstituted C₂ to C₆₀ heteroaryl group;—SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substitutedwith a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂ to C₆₀heteroaryl group, or two or more groups adjacent to each other bond toeach other to form a substituted or unsubstituted aliphatic or aromatichydrocarbon ring, and

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a substituted or unsubstitutedC₁ to C₆₀ alkyl group; a substituted or unsubstituted C₃ to C₆₀cycloalkyl group; a substituted or unsubstituted C₆ to C₆₀ aryl group;or a substituted or unsubstituted C₂ to C₆₀ heteroaryl group.

Another embodiment of the present application provides an organic lightemitting device comprising an anode, a cathode and one or more organicmaterial layers provided between the anode and the cathode, wherein oneor more layers of the organic material layers comprise the hetero-cycliccompound represented by Chemical Formula 1.

Advantageous Effects

A hetero-cyclic compound according to one embodiment of the presentapplication can be used as an organic material layer material of anorganic light emitting device. The hetero-cyclic compound can be used asa material of a hole injection layer, a hole transfer layer, a lightemitting layer, an electron transfer layer, an electron injection layer,a charge generation layer or the like in an organic light emittingdevice. Particularly, the hetero-cyclic compound represented by ChemicalFormula 1 can be used as a material of an electron transfer layer or acharge generation layer in an organic light emitting device. Inaddition, using the hetero-cyclic compound represented by ChemicalFormula 1 in an organic light emitting device lowers a driving voltageof the device, enhances light efficiency, and can enhance a lifespanproperty of the device with thermal stability of the compound.

DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 4 are diagrams each schematically illustrating alamination structure of an organic light emitting device according toone embodiment of the present application.

REFERENCE NUMERAL

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transfer Layer    -   303: Light Emitting Layer    -   304: Hole Blocking Layer    -   305: Electron Transfer Layer    -   306: Electron Injection Layer    -   400: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present application will be described in detail.

A hetero-cyclic compound according to one embodiment of the presentapplication is represented by Chemical Formula 1. More specifically, thehetero-cyclic compound represented by Chemical Formula 1 is capable ofbeing used as an organic material layer material of an organic lightemitting device with such a core structure and structuralcharacteristics of substituents.

In one embodiment of the present application, when m of Chemical Formula1 is 2 or greater, two or more L1s may be the same as or different fromeach other. In addition, when n of Chemical Formula 1 is 2 or greater,two or more Z1s may be the same as or different from each other.

In one embodiment of the present application, m of Chemical Formula 1may be an integer of 1 to 4.

In one embodiment of the present application, at least one of R1 to R5of Chemical Formula 1 may be represented by -(L2)p-(Z2)q. Herein, L2 hasthe same definition as L1 of Chemical Formula 1, Z2 has the samedefinition as Z1 of Chemical Formula 1, p is an integer of 0 to 4, and qis an integer of 1 to 4.

In another embodiment, one of R2 and R3 of Chemical Formula 1 may berepresented by -(L2)p-(Z2)q, and the other one may be hydrogen. Herein,L2 has the same definition as L1 of Chemical Formula 1, Z2 has the samedefinition as Z1 of Chemical Formula 1, p is an integer of 0 to 4, and qis an integer of 1 to 4.

According to one embodiment of the present application, Chemical Formula1 may be represented by the following Chemical Formula 2.

In Chemical Formula 2,

at least one of R1 to R5 is represented by -(L2)p-(Z2)q, and the resthave the same definitions as in Chemical Formula 1,

L2 has the same definition as L1 of Chemical Formula 1 and Z2 has thesame definition as Z1 of Chemical Formula 1,

p is an integer of 0 to 4,

q is an integer of 1 to 4, and

R6 to R11 have the same definitions as in Chemical Formula 1.

According to one embodiment of the present application, Chemical Formula1 may be represented by the following Chemical Formula 3.

In Chemical Formula 3,

at least one of R12 to R16 is represented by -(L3)r-(Z3)s, and the restare selected from the group consisting of hydrogen; deuterium; a halogengroup; —CN; a substituted or unsubstituted C₁ to C₆₀ alkyl group; asubstituted or unsubstituted C₆ to C₆₀ aryl group; a substituted orunsubstituted C₂ to C₆₀ heteroaryl group; —SiRR′R″; —P(═O)RR′; and anamine group unsubstituted or substituted with a C₁ to C₂₀ alkyl group, aC₆ to C₆₀ aryl group or a C₂ to C₆₀ heteroaryl group,

L3 has the same definition as L1 of Chemical Formula 1 and Z3 has thesame definition as Z1 of Chemical Formula 1,

r is an integer of 0 to 3,

s is an integer of 1 to 4, and

R6 to R11 have the same definitions as in Chemical Formula 1.

In one embodiment of the present application, at least one of R1 to R5of Chemical Formula 2 may be represented by -(L2)p-(Z2)q. Herein, L2 hasthe same definition as L1 of Chemical Formula 1, Z2 has the samedefinitions as Z1 of Chemical Formula 1, p is an integer of 0 to 4, andq is an integer of 1 to 4.

In another embodiment, one of R2 and R3 of Chemical Formula 2 may berepresented by -(L2)p-(Z2)q, and the other one may be hydrogen. Herein,L2 has the same definition as L1 of Chemical Formula 1, Z2 has the samedefinition as Z1 of Chemical Formula 1, p is an integer of 0 to 4, and qis an integer of 1 to 4.

In one embodiment of the present application, at least one of R12 to R16of Chemical Formula 3 may be represented by -(L3)r-(Z2)s. Herein, L3 hasthe same definition as L1 of Chemical Formula 1, Z3 has the samedefinition as Z1 of Chemical Formula 1, r is an integer of 0 to 3, and sis an integer of 1 to 4.

In another embodiment, one of R14 and R15 of Chemical Formula 3 may berepresented by -(L3)r-(Z3)s, and the other one may be hydrogen. Herein,L3 has the same definition as L1 of Chemical Formula 1, Z3 has the samedefinition as Z1 of Chemical Formula 1, r is an integer of 0 to 3, and sis an integer of 1 to 4.

In one embodiment of the present application, R6 to R11 of ChemicalFormulae 1 to 3 may be each independently hydrogen or deuterium.

In one embodiment of the present application, L1 to L3 of ChemicalFormulae 1 to 3 may be a direct bond; a substituted or unsubstituted C₆to C₆₀ arylene group; or a substituted or unsubstituted C₂ to C₆₀heteroarylene group.

In another embodiment, L1 to L3 of Chemical Formulae 1 to 3 may be adirect bond; a C₆ to C₄₀ arylene group; or a C₂ to C₄₀ heteroarylenegroup.

In another embodiment, L1 to L3 of Chemical Formulae 1 to may be adirect bond; a phenylene group; a divalent anthracene group; abiphenylene group; or a naphthalene group.

In one embodiment of the present application, Z1 to Z3 of ChemicalFormulae 1 to 3 may be each independently hydrogen; deuterium; asubstituted or unsubstituted C₆ to C₆₀ aryl group; or a substituted orunsubstituted C₂ to C₆₀ heteroaryl group.

In one embodiment of the present application, Z1 to Z3 of ChemicalFormulae 1 to 3 may be selected from the group consisting of hydrogen; asubstituted or unsubstituted C₁ to C₆₀ alkyl group; a substituted orunsubstituted C₆ to C₆₀ aryl group; a substituted or unsubstituted C₂ toC₆₀ heteroaryl group; and —P(═O)RR′.

In another embodiment, Z1 to Z3 of Chemical Formulae 1 to 3 may beselected from the group consisting of hydrogen; a substituted orunsubstituted C₆ to C₄₀ aryl group; a substituted or unsubstituted C₂ toC₄₀ N, O, S-containing heteroaryl group; and —P(═O)RR′.

In another embodiment, Z1 to Z3 of Chemical Formulae 1 to 3 may beselected from the group consisting of hydrogen; a C₆ to C₄₀ aryl groupunsubstituted or substituted with a C₆ to C₆₀ aryl group; a C₂ to C₄₀ N,O, S-containing heteroaryl group unsubstituted or substituted with oneor more substituents selected from the group consisting of a C₆ to C₆₀aryl group and a C₂ to C₆₀ heteroaryl group; and —P(═O)RR′.

In another embodiment, Z1 to Z3 of Chemical Formulae 1 to 3 may beselected from the group consisting of hydrogen; a phenyl group; anaphthyl group; a phenanthrene group; an anthracene group unsubstitutedor substituted with one or more substituents selected from the groupconsisting of a phenyl group and a naphthyl group; a phenanthrolinegroup unsubstituted or substituted with a phenyl group; a pyridine groupunsubstituted or substituted with a pyridine group; a pyrimidine groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a phenyl group, a biphenyl group, a naphthylgroup and a pyridine group; a triazine group unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of a phenyl group, a biphenyl group, a naphthyl group and apyridine group; a quinoline group; a carbazole group unsubstituted orsubstituted with a phenyl group; a dibenzofuran group; adibenzothiophene group; and —P(═O)RR′.

In one embodiment of the present application, R, R′ and R″ of ChemicalFormulae 1 to 3 are the same as or different from each other, and may beeach independently hydrogen; a substituted or unsubstituted C₁ to C₆₀alkyl group; or a substituted or unsubstituted C₆ to C₆₀ aryl group.

In another embodiment, R, R′ and R″ of Chemical Formulae 1 to 3 are thesame as or different from each other, and may be each independently aphenyl group.

In the present specification, the term “substituted or unsubstituted”means being substituted with one or more substituents selected from thegroup consisting of deuterium; a halogen group; —CN; a C₁ to C₆₀ alkylgroup; a C₂ to C₆₀ alkenyl group; a C₂ to C₆₀ alkynyl group; a C₃ to C₆₀cycloalkyl group; a C₂ to C₆₀ heterocycloalkyl group; a C₆ to C₆₀ arylgroup; a C₂ to C₆₀ heteroaryl group; —SiRR′R″; —P(═O)RR′; a C₁ to C₂₀alkylamine group; a C₆ to C₆₀ arylamine group; and a 02 to C₆₀heteroarylamine group, or being unsubstituted, or being substituted witha substituent bonding two or more of the above-mentioned substituents,or being substituted, or being substituted with a substituent linkingtwo or more substituents selected from among the above-mentionedsubstituents, or being unsubstituted. For example, “a substituentlinking two or more substituents” may comprise a biphenyl group. Inother words, a biphenyl group may be an aryl group, or may beinterpreted as a substituent linking two phenyl groups. The additionalsubstituents may be further substituted. R, R′ and R″ are the same as ordifferent from each other, and each independently hydrogen; deuterium;—CN; a substituted or unsubstituted C₁ to C₆₀ alkyl group; a substitutedor unsubstituted C₃ to C₆₀ cycloalkyl group; a substituted orunsubstituted C₆ to C₆₀ aryl group; or a substituted or unsubstituted C₂to C₆₀ heteroaryl group.

According to one embodiment of the present application, the “substitutedor unsubstituted” means being substituted with one or more substituentsselected from the group consisting of deuterium, a halogen group, —CN,SiRR′R″, P(═O)RR′, a C₁ to C₂₀ linear or branched alkyl group, a C₆ toC₆₀ aryl group, and a C₂ to C₆₀ heteroaryl group, or beingunsubstituted, and

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a C₁ to C₆₀ alkyl groupunsubstituted or substituted with deuterium, a halogen group, —CN, a C₁to C₂₀ alkyl group, a C₆ to C₆₀ aryl group and a C₂ to C₆₀ heteroarylgroup; a C₃ to C₆₀ cycloalkyl group unsubstituted or substituted withdeuterium, halogen, —CN, a C₁ to C₆₀ alkyl group, a C₆ to C₆₀ aryl groupand a C₂ to C₆₀ heteroaryl group; a C₆ to C₆₀ aryl group unsubstitutedor substituted with deuterium, halogen, —CN, a C₁ to C₂₀ alkyl group, aC₆ to C₆₀ aryl group and a C₂ to C₆₀ heteroaryl group; or a C₂ to C₆₀heteroaryl group unsubstituted or substituted with deuterium, halogen,—CN, a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group and a C₂ to C₆₀heteroaryl group.

The term “substituted” means a hydrogen atom bonding to a carbon atom ofa compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which thehydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

In the present specification, the halogen may be fluorine, chlorine,bromine or iodine.

In the present specification, the alkyl group comprises linear orbranched having 1 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkyl groupmay be from 1 to 60, specifically from 1 to 40 and more specificallyfrom 1 to 20. Specific examples thereof may comprise a methyl group, anethyl group, a propyl group, an n-propyl group, an isopropyl group, abutyl group, an n-butyl group, an isobutyl group, a tert-butyl group, asec-butyl group, a 1-methyl-butyl group, a 1-ethylbutyl group, a pentylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, atert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentylgroup, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, ann-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propylgroup, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group and the like, butare not limited thereto.

In the present specification, the alkenyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkenyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20. Specific examples thereof may comprise a vinyl group, a1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, anallyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-ylgroup, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, astyrenyl group and the like, but are not limited thereto.

In the present specification, the alkynyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkynyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20.

In the present specification, the cycloalkyl group comprises monocyclicor multicyclic having 3 to 60 carbon atoms, and may be furthersubstituted with other substituents. Herein, the multicyclic means agroup in which the cycloalkyl group is directly linked to or fused withother cyclic groups. Herein, the other cyclic groups may be a cycloalkylgroup, however, may also be different types of cyclic groups such as aheterocycloalkyl group, an aryl group and a heteroaryl group. The numberof carbon groups of the cycloalkyl group may be from 3 to 60,specifically from 3 to 40 and more specifically from 5 to 20. Specificexamples thereof may comprise a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a 3-methylcyclopentyl group, a2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexylgroup, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, acycloheptyl group, a cyclooctyl group and the like, but are not limitedthereto.

In the present specification, the heterocycloalkyl group comprises O, S,Se, N or Si as a heteroatom, comprises monocyclic or multicyclic having2 to 60 carbon atoms, and may be further substituted with othersubstituents. Herein, the multicyclic means a group in which theheterocycloalkyl group is directly linked to or fused with other cyclicgroups. Herein, the other cyclic groups may be a heterocycloalkyl group,however, may also be different types of cyclic groups such as acycloalkyl group, an aryl group and a heteroaryl group. The number ofcarbon atoms of the heterocycloalkyl group may be from 2 to 60,specifically from 2 to 40 and more specifically from 3 to 20.

In the present specification, the aryl group comprises monocyclic ormulticyclic having 6 to 60 carbon atoms, and may be further substitutedwith other substituents. Herein, the multicyclic means a group in whichthe aryl group is directly linked to or fused with other cyclic groups.Herein, the other cyclic groups may be an aryl group, however, may alsobe different types of cyclic groups such as a cycloalkyl group, aheterocycloalkyl group and a heteroaryl group. The aryl group comprisesa spiro group. The number of carbon atoms of the aryl group may be from6 to 60, specifically from 6 to 40 and more specifically from 6 to 25.Specific examples of the aryl group may comprise a phenyl group, abiphenyl group, a triphenyl group, a naphthyl group, an anthryl group, achrysenyl group, a phenanthrenyl group, a perylenyl group, afluoranthenyl group, a triphenylenyl group, a phenalenyl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a fusedring thereof, and the like, but are not limited thereto.

In the present specification, the spiro group is a group comprising aspiro structure, and may have 15 to 60 carbon atoms. For example, thespiro group may comprise a structure in which a 2,3-dihydro-1H-indenegroup or a cyclohexane group spiro bonds to a fluorenyl group.Specifically, the following Spiro group may comprise any one of thegroups having the following structural formulae.

In the present specification, the heteroaryl group comprises O, S, Se, Nor Si as a heteroatom, comprises monocyclic or multicyclic having 2 to60 carbon atoms, and may be further substituted with other substituents.Herein, the multicyclic means a group in which the heteroaryl group isdirectly linked to or fused with other cyclic groups. Herein, the othercyclic groups may be a heteroaryl group, however, may also be differenttypes of cyclic groups such as a cycloalkyl group, a heterocycloalkylgroup and an aryl group. The number of carbon atoms of the heteroarylgroup may be from 2 to 60, specifically from 2 to 40 and morespecifically from 3 to 25. Specific examples of the heteroaryl group maycomprise a pyridyl group, a pyrrolyl group, a pyrimidyl group, apyridazinyl group, a furanyl group, a thiophene group, an imidazolylgroup, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, atriazolyl group, an isothiazolyl group, a triazolyl group, a furazanylgroup, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group,a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinylgroup, an oxazinyl group, a triazinyl group, a dioxynyl group, atriazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolylgroup, a quinazolinyl group, an isoquinazolinyl group, a qninozolinylgroup, a naphthyridyl group, an acridinyl group, a phenanthridinylgroup, an imidazopyridinyl group, a diazanaphthalenyl group, atriazaindene group, an indolyl group, an indolizinyl group, abenzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, abenzothiophene group, a benzofuran group, a dibenzothiophene group, adibenzofuran group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a phenazinyl group, a dibenzosilole group,spirobi(dibenzosilole), a dihydrophenazinyl group, a phenoxazinyl group,a phenanthridyl group, an imidazopyridinyl group, a thienyl group, anindolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, anindolinyl group, a 10,11-dihydro-dibenzo[b,f]azepine group, a9,10-dihydroacridinyl group, a phenanthrazinyl group, aphenothiathiazinyl group, a phthalazinyl group, a naphthylidinyl group,a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrobenzo[b,e][1,4]azasilinyl, a pyrazolo[1,5-c]quinazolinylgroup, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, a5,11-dihydroindeno[1,2-b]carbazolyl group and the like, but are notlimited thereto.

In the present specification, the amine group may be selected from thegroup consisting of a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 1 to 30. Specific examples of the amine group maycomprise a methylamine group, a dimethylamine group, an ethylaminegroup, a diethylamine group, a phenylamine group, a naphthylamine group,a biphenylamine group, a dibiphenylamine group, an anthracenylaminegroup, a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group andthe like, but are not limited thereto.

In the present specification, the arylene group means the aryl grouphaving two bonding sites, that is, a divalent group. Descriptions on thearyl group provided above may be applied thereto except for each being adivalent. In addition, the heteroarylene group means the heteroarylgroup having two bonding sites, that is, a divalent group. Descriptionson the heteroaryl group provided above may be applied thereto except foreach being a divalent.

According to one embodiment of the present application, Chemical Formula1 may be represented by any one of the following compounds, but is notlimited thereto.

In addition, by introducing various substituents to the structure ofChemical Formula 1, compounds having unique properties of the introducedsubstituents may be synthesized. For example, by introducingsubstituents normally used as hole injection layer materials, holetransfer layer materials, light emitting layer materials, electrontransfer layer materials and charge generation layer materials used formanufacturing an organic light emitting device to the core structure,materials satisfying conditions required for each organic material layermay be synthesized.

In addition, by introducing various substituents to the structure ofChemical Formula 1, the energy band gap may be finely controlled, andmeanwhile, properties at interfaces between organic materials areenhanced, and material applications may become diverse.

Meanwhile, the hetero-cyclic compound has excellent thermal stabilitywith a high glass transition temperature (Tg). Such an increase in thethermal stability becomes an important factor in providing drivingstability to a device.

The hetero-cyclic compound according to one embodiment of the presentapplication may be prepared through a multistep chemical reaction. Someintermediate compounds are prepared first, and the compound of ChemicalFormula 1 may be prepared from the intermediate compounds. Morespecifically, the hetero-cyclic compound according to one embodiment ofthe present application may be prepared based on preparation examples tobe described below.

Another embodiment of the present application provides an organic lightemitting device comprising the hetero-cyclic compound represented byChemical Formula 1.

The organic light emitting device according to one embodiment of thepresent application may be manufactured using common organic lightemitting device manufacturing methods and materials except that one ormore organic material layers are formed using the hetero-cyclic compounddescribed above.

The hetero-cyclic compound may be formed into an organic material layerthrough a solution coating method as well as a vacuum deposition methodwhen manufacturing the organic light emitting device. Herein, thesolution coating method means spin coating, dip coating, inkjetprinting, screen printing, a spray method, roll coating and the like,but is not limited thereto.

Specifically, the organic light emitting device according to oneembodiment of the present application comprises an anode, a cathode, andone or more organic material layers provided between the anode and thecathode, wherein one or more layers of the organic material layerscomprise the hetero-cyclic compound represented by Chemical Formula 1.

FIGS. 1 to 3 illustrate a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to oneembodiment of the present application. However, the scope of the presentapplication is not limited to these diagrams, and structures of organiclight emitting devices known in the art may also be used in the presentapplication.

FIG. 1 illustrates an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) areconsecutively laminated on a substrate (100). However, the structure isnot limited to such a structure, and as illustrated in FIG. 2, anorganic light emitting device in which a cathode, an organic materiallayer and an anode are consecutively laminated on a substrate may alsobe obtained.

FIG. 3 illustrates a case of the organic material layer being amultilayer. The organic light emitting device according to FIG. 3comprises a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), a hole blocking layer (304), an electrontransfer layer (305) and an electron injection layer (306). However, thescope of the present application is not limited to such a laminationstructure, and as necessary, other layers except the light emittinglayer may not be included, and other necessary functional layers may befurther included.

In addition, the organic light emitting device according to oneembodiment of the present application comprises an anode, a cathode, andtwo or more stacks provided between the anode and the cathode, whereinthe two or more stacks each independently comprise a light emittinglayer, a charge generation layer is included between the two or morestacks, and the charge generation layer comprises the hetero-cycliccompound represented by Chemical Formula 1.

In addition, the organic light emitting device according to oneembodiment of the present application comprises an anode, a first stackprovided on the anode and comprising a first light emitting layer, acharge generation layer provided on the first stack, a second stackprovided on the charge generation layer and comprising a second lightemitting layer, and a cathode provided on the second stack. Herein, thecharge generation layer may comprise the hetero-cyclic compoundrepresented by Chemical Formula 1. In addition, the first stack and thesecond stack may each independently further comprise one or more typesof the hole injection layer, the hole transfer layer, the hole blockinglayer, the electron transfer layer, the electron injection layerdescribed above and the like.

The charge generation layer may be an N-type charge generation layer,and the charge generation layer may further comprise a dopant known inthe art in addition to the hetero-cyclic compound represented byChemical Formula 1.

As the organic light emitting device according to one embodiment of thepresent application, an organic light emitting device having a 2-stacktandem structure is schematically illustrated in FIG. 4.

Herein, the first electron blocking layer, the first bole blockinglayer, the second hole blocking layer and the like described in FIG. 4may not be included in some cases.

The organic light emitting device according to the present specificationmay be manufactured using materials and methods known in the art exceptthat one or more layers of the organic material layers comprise thehetero-cyclic compound represented by Chemical Formula 1.

The hetero-cyclic compound represented by Chemical Formula 1 may formone or more layers of the organic material layers of the organic lightemitting device alone. However, as necessary, the hetero-cyclic compoundrepresented by Chemical Formula 1 may be mixed with other materials toform the organic material layers.

The hetero-cyclic compound represented by Chemical Formula 1 may be usedas a material of the charge generation layer in the organic lightemitting device.

The hetero-cyclic compound represented by Chemical Formula 1 may be usedas a material of the electron transfer layer, the hole blocking layer,the light emitting layer or the like in the organic light emittingdevice. As one example, the hetero-cyclic compound represented byChemical Formula 1 may be used as a material of the electron transferlayer, the hole transfer layer or the light emitting layer in theorganic light emitting device.

In addition, the hetero-cyclic compound represented by Chemical Formula1 may be used as a material of the light emitting layer in the organiclight emitting device. As one example, the hetero-cyclic compoundrepresented by Chemical Formula 1 may be used as a phosphorescent hostmaterial of the light emitting layer in the organic light emittingdevice.

In the organic light emitting device according to one embodiment of thepresent application, materials other than the hetero-cyclic compound ofChemical Formula 1 are illustrated below, however, these are forillustrative purposes only and not for limiting the scope of the presentapplication, and may be replaced by materials known in the art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used. Specific examples of the anodematerial comprise metals such as vanadium, chromium, copper, zinc andgold, or alloys thereof; metal oxides such as zinc oxide, indium oxide,indium tin oxide (ITO) and indium zinc oxide (IZO); combinations ofmetals and oxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylcompound), poly[3,4-(ethylene-1,2-dioxy)compound] (PEDOT),polypyrrole and polyaniline, but are not limited thereto.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used. Specific examples of the cathode material comprise metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the hole injection material, known hole injection materials may beused, and for example, phthalocyanine compounds such as copperphthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-typeamine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA),4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB)described in the literature [Advanced Material, 6, p. 677 (1994)],polyaniline/dodecylbenzene sulfonic acid,poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate),polyaniline/camphor sulfonic acid orpolyaniline/poly(4-styrene-sulfonate) that are conductive polymershaving solubility, and the like, may be used.

As the hole transfer material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives and thelike may be used, and low molecular or high molecular materials may alsobe used.

As the electron transfer material, metal complexes of oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinolineand derivatives thereof, and the like, may be used, and high molecularmaterials may also be used as well as low molecular materials.

As examples of the electron injection material, LiF is typically used inthe art, however, the present application is not limited thereto.

As the light emitting material, red, green or blue light emittingmaterials may be used, and as necessary, two or more light emittingmaterials may be mixed and used. In addition, fluorescent materials mayalso be used as the light emitting material, however, phosphorescentmaterials may also be used. As the light emitting material, materialsemitting light by bonding electrons and holes injected from an anode anda cathode, respectively, may be used alone, however, materials having ahost material and a dopant material involved in light emission togethermay also be used.

The organic light emitting device according to one embodiment of thepresent application may be a top-emission type, a bottom-emission typeor a dual-emission type depending on the materials used.

The hetero-cyclic compound according to one embodiment of the presentapplication may also be used in an organic electronic device comprisingan organic solar cell, an organic photo conductor, an organic transistorand the like under a similar principle used in the organic lightemitting device.

Hereinafter, the present specification will be described in more detailwith reference to examples, however, these are for illustrative purposesonly, and the scope of the present application is not limited thereto.

EXAMPLE <Preparation Example 1> Preparation of Compound 1

1) Preparation of Compound 1-1

Nitromethane (600 ml) was introduced to naphthalen-2-amine (60 g, 419.02mmol, 1 eq.), 4-bromobenzaldehyde (77.5 g, 419.02 mmol, 1 eq.) andethynylbenzene (64.2 g, 628.54 mmol, 1.5 eq.), iodine (10.6 g, 41.90mmol, 0.1 eq.) was added thereto, and the result was stirred at 100° C.

MC was added to the reaction solution and dissolved, the result wasextracted with water, and the organic layer was dried with anhydrousNa₂SO₄.

The result was separated using a silica-gel column (developing solventEA:Hex=1:10→MC:EA=1:1).

The result was precipitated using MC/Hex→MC/MeOH to obtain 46 g ofCompound 1-1 in a 27% yield.

2) Preparation of Compound 1-2

After dissolving Compound 1-1 (25 g, 60.93 mmol, 1 eq.) andbis(pinacolato)diboron (23.2 g, 91.39 mmol, 1.5 eq.) in 1,4-dioxane (250ml), (N₂ condition) PdCl₂(dppf) (2.2 g, 3.05 mmol, 0.05 eq.) and KOAc(23.9 g, 243.72 mmol, 4 eq.) were added thereto, and the result wasstirred for 6 hours at 100° C.

After extracting the result with MC and water, the organic layer wasdried with anhydrous Na₂SO₄, and the result was silica-gel filtered.

The result was precipitated using MC/MeOH. The precipitates werefiltered to obtain 24.5 g of Compound 1-2 in a 88% yield.

3) Preparation of Compound 1

After dissolving Compound 1-2 (20.1 g, 43.95 mmol, 1 eq.) and2-bromo-1,10-phenanthroline (11.4 g, 43.95 mmol, 1 eq.) in 200 ml ofTol, 40 ml of EtOH and 40 ml of H₂O, (N₂ condition) Pd(PPh₃)₄ (2.5 g,2.20 mmol, 0.05 eq.) and K₂CO₃ (12.2 g, 87.89 mmol, 2 eq.) were addedthereto, and the result was stirred under reflux for 15 hours.

MC was introduced to the reaction solution and dissolved, the result wasextracted with water, and the organic layer was dried with anhydrousNa₂SO₄.

The result was silica-gel filtered, and precipitated using MC/MeOH andMC/acetone.

The result was soxhlet extracted to obtain 10.47 g of Compound 1 in a47% yield.

Target Compound A was synthesized in the same manner using, inPreparation Example 1, Intermediate A of the following Table 1 insteadof 2-bromo-1,10-phenanthroline.

TABLE 1 Compound Number Intermediate A Target Compound A Yield  2

65%  3

71%  5

69%  15

83%  25

78%  35

67%  45

70%  46

62%  50

84%  52

71% 102

74%

<Preparation Example 2> Preparation of Compound 149

1) Preparation of Compound 149-1

Nitromethane (600 ml) was introduced to naphthalen-2-amine (60 g, 419.02mmol, 1 eq.), 3-bromobenzaldehyde (77.5 g, 419.02 mmol, 1 eq.) andethynylbenzene (64.2 g, 628.54 mmol, 1.5 eq.), iodine (10.6 g, 41.90mmol, 0.1 eq.) was added thereto, and the result was stirred at 100° C.

MC was added to the reaction solution and dissolved, the result wasextracted with water, and the organic layer was dried with anhydrousNa₂SO₄.

The result was separated using a silica-gel column (developing solventEA:Hex=1:10→MC:EA→1:1).

The result was precipitated using MC/Hex→MC/MeOH to obtain 62 g ofCompound 149-1 in a 36% yield.

2) Preparation of Compound 149-2

After dissolving Compound 149-1 (25 g 60.93 mmol, 1 eq.) andbis(pinacolato)diboron (23.2 g, 91.39 mmol, 1.5 eq.) in 1,4-dioxane (250ml), (N₂ condition) PdCl₂(dppf) (2.2 g, 3.05 mmol, 0.05 eq.) and KOAc(23.9 g, 243.72 mmol, 4 eq.) were added thereto, and the result wasstirred for 6 hours at 100° C.

After extracting the result with MC and water, the organic layer wasdried with anhydrous Na₂SO₄, and the result was silica-gel filtered.

The result was precipitated using MC/MeOH. The precipitates werefiltered to obtain 24 g of Compound 149-2 in a 86% yield.

3) Preparation of Compound 149

After dissolving Compound 149-2 (20.1 g, 43.95 mmol, 1 eq.) and2-bromo-1,10-phenanthroline (11.4 g, 43.95 mmol, 1 eq.) in 200 ml ofTol, 40 ml of EtOH and 40 ml of H₂O, (N₂ condition) Pd(PPh₃)₄ (2.5 g,2.20 mmol, 0.05 eq.) and K₂CO₃ (12.2 g, 87.89 mmol, 2 eq.) were addedthereto, and the result was stirred under reflux for 15 hours.

MC was introduced to the reaction solution and dissolved, the result wasextracted with water, and the organic layer was dried with anhydrousNa₂SO₄.

The result was silica-gel filtered, and precipitated using MC/MeOH andMC/acetone.

The result was soxhlet extracted to obtain 16 g of Compound 149 in a 71%yield.

Target Compound B was synthesized in the same manner using, inPreparation Example 2, Intermediate B of the following Table 2 insteadof 2-bromo-1,10-phenanthroline.

TABLE 2 Compound Number Intermediate B Target Compound B Yield 150

69% 151

73% 153

64% 163

88% 173

72% 183

69% 194

69% 198

81% 199

73% 555

81%

<Preparation Example 3> Preparation of Compound 249

1) Preparation of Compound 249-1

Tetrahydrofuran (375 mL) and distilled water (3.75 mL) were introducedto naphthalen-2-amine (15 g, 0.104 mol, 1 eq.), 4-bromoacetophenone(20.75 g, 0.104 mol, 1 eq.) and benzaldehyde (11.12 g, 0.104 mol, 1.5eq.), iodine (1.3 g, 0.0052 mol, 0.05 eq.) was added thereto, and theresult was stirred at 80° C.

After removing the solvent from the reaction solution, Na₂S₂O₃,distilled water and acetone were added thereto, and the produced solidswere filtered and washed with acetone to obtain 16 g of Compound 249-1in a 38% yield.

2) Preparation of Compound 249-2

After dissolving Compound 249-1 (16 g, 0.0389 mol, 1 eq.) andbis(pinacolato)diboron (14.8 g, 0.0584 mol, 1.5 eq.) in 1,4-dioxane (240ml), (N₂ condition) PdCl₂(dppf) (2.8 g, 0.0038 mol, 0.1 eq.) and KOAc(11.48 g, 0.116 mol, 3 eq.) were added thereto, and the result wasstirred for 14 hours at 100° C.

After terminating the reaction using H₂O, the produced solids werefiltered. The solids were dissolved in MC, silica-gel adsorbed, andcolumn separated (developing solvent MC:Hex 1:1). After removing thesolvent, the result was precipitated using MC/MeOH. The precipitateswere filtered to obtain 13 g of Compound 249-2 in a 73% yield.

3) Preparation of Compound 249

After dissolving Compound 249-2 (13 g, 0.028 mol, 1 eq.) and2-bromo-1,10-phenanthroline (7.36 g, 0.028 mol, 1 eq.) in 160 ml of Tol,40 ml of EtOH and 40 ml of H₂O, (N₂ condition) Pd(PPh₃)₄ (1.6 g, 0.0014mol, 0.05 eq.) and K₂CO₃ (7.85 g, 0.056 mol, 2 eq.) were added thereto,and the result was stirred under reflux for 8 hours.

MC was introduced to the reaction solution and dissolved, the result wasextracted with water, and the organic layer was dried with anhydrousNa₂SO₄.

The result was silica-gel filtered, and precipitated using MC/MeOH andMC/acetone.

The result was soxhlet extracted to obtain 11 g of Compound 249 in a 76%yield.

Target Compound C was synthesized in the same manner using, inPreparation Example 3, Intermediate C of the following Table 3 insteadof 2-bromo-1,10-phenanthroline.

TABLE 3 Compound Number Intermediate C Target Compound C Yield 344

65% 345

70% 556

72%

Compounds were prepared in the same manner as in the preparationexamples, and the synthesis identification results are shown in Table 4and Table 5. Table 4 shows measurement values of ¹H NMR (CDCl₃, 200MHz), and Table 5 shows measurement values of field desorption massspectrometry (FD-MS).

TABLE 4 Compound ¹H NMR (CDCl₃, 200 Mz) 1 δ = 8.84 (4H, dd), 8.83 (1H,d), 8.54 (1H, d), 8.38 (1H, d), 8.16 (1H, d), 8.10 (1H, d), 8.06 (1H,d), 7.99~7.98 (2H, m), 7.81~7.79 (3H, m), 7.67 (2H, m), 7.64 (1H, s),7.58 (1H, m), 7.51 (2H, m), 7.41 (1H, m), 7.35 (1H, d) 2 δ = 8.84 (4H,dd), 8.54 (1H, d), 8.30 (2H, d), 8.16~8.06 (4H, m), 7.99~7.79 (5H, m),7.67~7.64 (3H, m), 7.54~7.51 (4H, m), 7.47~7.41 (2H, m), 7.35 (2H, m) 3δ = 8.83~8.81 (4H, m), 8.54 (1H, m), 8.38 (2H, m), 8.16 (1H, d),7.99~7.98 (2H, m), 7.79 (2H, d), 7.67~7.64 (4H, m), 7.58~7.51 (4H, m),7.41 (1H, m), 7.28 (2H, d) 5 δ = 8.81 (2H, d), 8.54 (1H, d), 8.23 (1H,s), 8.16 (1H, d), 7.99~7.98 (2H, dd), 7.88 (2H, d), 7.79 (6H, m),7.67~7.64 (3H, m), 7.51 (6H, m), 7.41 (3H, m) 15 δ = 8.81 (2H, d), 8.54(1H, d), 8.33~8.23 (5H, m), 8.16 (1H, d), 7.99~7.98 (2H, m), 7.79~7.64(7H, m), 7.51 (6H, m), 7.41 (3H, m) 25 δ = 8.81 (2H, d), 8.54 (1H, d),8.28 (4H, m), 8.16 (1H, m), 7.99~7.98 (2H, m), 7.88 (2H, d), 7.79 (2H,m), 7.67~7.64 (3H, m), 7.51 (6H, m), 7.41 (3H, m) 35 δ = 9.30~9.15 (4H,m), 8.81 (2H, d), 8.54~8.53 (3H, m), 8.16 (1H, m), 7.99~7.88 (4H, m),7.79~7.64 (7H, m), 7.51 (2H, m), 7.14 (3H, m) 45 δ = 8.93 (2H, d), 8.81(2H, d), 7.89 (1H, m), 8.16 (3H, m), 7.98~7.79 (9H, m), 7.67 (3H, m),7.51 (3H, m), 7.28 (2H, m) 46 δ = 8.54 (1H, m), 8.30 (2H, d), 8.16 (1H,m), 7.99~7.98 (2H, m), 7.86~7.77 (8H, m), 7.67~7.64 (3H, m), 7.51 (2H,m), 7.45~7.41 (7H, m) 50 δ = 8.81 (2H, d), 8.55~8.54 (3H, m), 8.16~8.09(5H, m), 7.99~7.94 (4H, m), 7.88~7.79 (4H, m), 7.67~7.63 (5H, m),7.51~7.50 (4H, m), 7.41~7.40 (2H, m), 7.33~7.29 (4H, m), 7.25 (2H, m) 52δ = 8.81 (4H, m), 8.54 (1H, m), 8.30 (2H, m), 8.16~7.98 (6H, m),7.88~7.79 (7H, m), 7.67~7.51 (7H, m), 7.47~7.35 (4H, m) 102 δ = 8.81(2H, d), 8.55~8.22 (4H, m), 8.30 (2H, m), 8.16~7.98 (7H, m), 7.81~7.79(3H, m), 7.67~7.64 (3H, m), 7.55~7.41 (8H, m), 7.35~7.28 (4H, m) 149 δ =8.83 (1H, d), 8.72 (1H, s), 8.54 (1H, m), 8.38~8.32 (3H, m), 8.16~8.06(3H, m), 7.99~7.98 (2H, dd), 7.81~7.79 (3H, m), 7.67~7.63 (4H, m),7.58~7.51 (3H, m), 7.41~7.35 (2H, m) 150 δ = 8.72 (1H, s), 8.54 (1H, m),8.32~8.30 (4H, m), 8.16~7.98 (6H, m), 7.81~7.79 (3H, m), 7.67~7.35 (12H,m) 151 δ = 8.83 (2H, d), 8.54 (1H, m), 8.38 (2H, dd), 8.26~8.16 (3H, m),7.99~7.98 (2H, m), 7.79 (2H, m), 7.67~7.41 (11H, m) 153 δ = 8.54 (1H,m), 8.30~8.16 (5H, m), 7.99~7.98 (2H, dd), 7.79 (613, dd), 7.67~7.41(13H, m) 163 δ = 8.54 (1H, m), 8.28~8.16 (6H, m), 7.99~7.98 (2H, dd),7.81~7.79 (5H, m), 7.67~7.41 (13H, m) 173 δ = 8.54 (1H, m), 8.30~8.16(8H, m), 7.99~7.98 (2H, m), 7.79 (2H, m), 7.67~7.41 (13H, m) 183 δ =9.30 (2H, dd), 9.15 (2H, s), 8.54~8.53 (3H, m), 8.26~8.16 (3H, m),7.99~7.98 (2H, m), 7.79~7.41 (12H, m), 7.14 (2H, m) 194 δ = 8.54 (1H,m), 8.30 (1H, dd), 8.17~8.16 (2H, m), 7.99~7.98 (2H, m), 7.79~7.77 (7H,m), 7.67~7.64 (3H, m), 7.54~7.41 (10H, s) 198 δ = 8.55~8.54 (3H, m),8.26~8.09 (7H, m), 7.99~7.94 (4H, m), 7.79 (2H, m), 7.67~7.25 (19H, m)199 δ = 8.81 (2H, dd), 8.54 (1H, dd), 8.30~7.98 (10H, m), 7.88~7.79 (5H,m), 7.67~7.35 (13H, m) 249 δ = 8.81 (3H, m), 8.54 (1H, dd), 8.38 (3H,m), 8.16~7.98 (5H, m), 7.81 (1H, dd) 7.64~7.47 (7H, m) 7.28 (3H, m) 344δ = 8.54 (1H, d), 8.30 (2H, m), 8.16 (1H, d), 7.98 (2H, d) 7.79~7.45(20H, m), 7.25 (4H, m) 345 δ = 8.55 (2H, m), 8.30 (2H, m), 8.16 (2H, m),7.98 (3H, m) 7.79 (2H, m) 7.67~7.54 (10H, m), 7.29 (7H, m) 555 δ =8.55~8.52 (4H, m), 8.30~7.98 (11H, m), 7.81~7.79 (3H, m), 7.67~7.35(15H, m) 556 δ = 8.54 (1H, d), 8.30 (2H, dd), 8.16 (1H, d), 7.91 (6H, m)7.64~7.39 (15H, m) 7.25 (8H, m)

TABLE 5 Compound FD-MS Compound FD-MS 1 m/z = 509.60 2 m/z = 585.69(C37H23N3 = 509.19) (C43H27N3 = 585.22) 3 m/z = 509.60 4 m/z = 661.79(C37H23N3 = 509.19) (C49H31N3 = 661.25) 5 m/z = 561.67 6 m/z = 637.77(C41H27N3 = 561.22) (C47H31N3 = 637.25) 7 m/z = 713.87 8 m/z = 661.79(C53H35N3 = 713.28) (C49H31N3 = 661.25) 9 m/z = 661.79 10 m/z = 637.77(C49H31N3 = 661.25) (C47H31N3 = 637.25) 11 m/z = 713.87 12 m/z = 563.65(C53H35N3 = 713.28) (C39H25N5 = 563.21) 13 m/z = 563.65 14 m/z = 563.65(C39H25N5 = 563.21) (C39H25N5 = 563.21) 15 m/z = 561.67 16 m/z = 637.77(C41H27N3 = 561.22) (C47H31N3 = 637.25) 17 m/z = 713.87 18 m/z = 661.79(C53H35N3 = 713.28) (C49H31N3 = 661.25) 19 m/z = 661.79 20 m/z = 637.77(C49H31N3 = 661.25) (C47H31N3 = 637.25) 21 m/z = 713.87 22 m/z = 563.65(C53H35N3 = 713.28) (C39H25N5 = 563.21) 23 m/z = 563.65 24 m/z = 563.65(C39H25N5 = 563.21) (C39H25N5 = 563.21) 25 m/z = 562.66 26 m/z = 638.76(C40H26N4 = 562.22) (C46H30N4 = 638.25) 27 m/z = 714.85 28 m/z = 662.78(C52H34N4 = 714.28) (C48H30N4 = 662.25) 29 m/z = 662.78 30 m/z = 585.69(C48H30N4 = 662.25) (C46H30N4 = 638.25) 31 m/z = 714.85 32 m/z = 564.64(C52H34N4 = 714.28) (C38H24N6 = 564.21) 33 m/z = 564.64 34 m/z = 564.64(C38H24N6 = 564.21) (C38H24N6 = 564.21) 35 m/z = 562.66 36 m/z = 458.55(C40H26N4 = 562.22) (C34H22N2 = 458.18) 37 m/z = 458.55 38 m/z = 458.55(C34H22N2 = 458.18) (C34H22N2 = 458.18) 39 m/z = 458.55 40 m/z = 458.55(C34H22N2 = 458.18) (C34H22N2 = 458.18) 41 m/z = 583.72 42 m/z = 633.78(C45H29N = 583.23) (C49H31N = 633.25) 43 m/z = 659.81 44 m/z = 759.93(C51H33N = 659.26) (C59H37N = 759.29) 45 m/z = 507.62 46 m/z = 531.58(C39H25N = 507.20) (C37H26NOP = 531.18) 47 m/z = 496.60 48 m/z = 572.70(C37H24N23 = 496.19) (C43H28N2 = 572.23) 49 m/z = 572.70 50 m/z = 737.89(C43H28N2 = 572.23) (C55H35N3 = 737.28) 51 m/z = 585.69 52 m/z = 661.79(C43H27N3 = 585.22) (C49H31N3 = 661.25) 53 m/z = 585.69 54 m/z = 737.89(C43H27N3 = 585.22) (C55H35N3 = 737.28) 55 m/z = 637.77 56 m/z = 713.87(C47H31N3 = 637.25) (C53H35N3 = 713.28) 57 m/z = 789.96 58 m/z = 737.89(C59H39N3 = 789.31) (C55H35N3 = 737.28) 59 m/z = 737.89 60 m/z = 713.87(C55H35N3 = 737.28) (C53H35N3 = 713.28) 61 m/z = 789.96 62 m/z = 639.75(C59H39N3 = 789.31) (C45H29N5 = 639.24) 63 m/z = 639.75 64 m/z = 639.75(C45H29N5 = 639.24) (C45H29N5 = 639.24) 65 m/z = 637.77 66 m/z = 713.87(C47H31N3 = 637.25) (C53H35N3 = 713.28) 67 m/z = 789.96 68 m/z = 737.89(C59H39N3 = 789.31) (C55H35N3 = 737.28) 69 m/z = 737.89 70 m/z = 713.87(C55H35N3 = 737.28) (C53H35N3 = 713.28) 71 m/z = 789.96 72 m/z = 639.75(C59H39N3 = 789.31) (C45H29N5 = 639.24) 73 m/z = 639.75 74 m/z = 639.75(C45H29N5 = 639.24) (C45H29N5 = 639.24) 75 m/z = 638.76 76 m/z = 714.85(C46H30N4 = 638.25) (C52H34N4 = 714.28) 77 m/z = 790.95 78 m/z = 738.87(C58H38N4 = 790.31) (C54H34N4 = 738.28) 79 m/z = 738.87 80 m/z = 714.85(C54H34N4 = 738.28) (C52H34N4 = 714.28) 81 m/z = 790.95 82 m/z = 640.73(C58H38N4 = 790.31) (C44H28N6 = 640.24) 83 m/z = 640.73 84 m/z = 640.73(C44H28N6 = 640.24) (C44H28N6 = 640.24) 85 m/z = 638.76 86 m/z = 534.65(C46H30N4 = 638.25) (C40H26N2 = 534.21) 87 m/z = 534.65 88 m/z = 534.65(C40H26N2 = 534.21) (C40H26N2 = 534.21) 89 m/z = 534.65 90 m/z = 534.65(C40H26N2 = 534.21) (C40H26N2 = 534.21) 91 m/z = 659.81 92 m/z = 709.87(C51H33N = 659.26) (C55H35N = 709.28) 93 m/z = 735.91 94 m/z = 836.03(C57H37N = 735.29) (C65H41N = 835.32) 95 m/z = 583.72 96 m/z = 607.68(C45H29N = 583.23) (C43H30NOP = 607.21) 97 m/z = 572.70 98 m/z = 648.79(C43H28N2 = 572.23) (C49H32N2 = 648.26) 99 m/z = 648.79 100 m/z = 813.98(C49H32N2 = 648.26) (C61H39N3 = 813.31) 101 m/z = 635.75 102 m/z =711.85 (C47H29N3 = 635.24) (C53H33N3 = 711.27) 103 m/z = 635.75 104 m/z= 787.95 (C47H29N3 = 635.24) (C59H37N3 = 787.30) 105 m/z = 687.83 106m/z = 763.92 (C51H33N3 = 687.27) (C57H37N3 = 763.30) 107 m/z = 840.02108 m/z = 787.95 (C63H41N3 = 839.33) (C59H37N3 = 787.30) 109 m/z =787.95 110 m/z = 763.92 (C59H37N3 = 787.30) (C57H37N3 = 763.30) 111 m/z= 840.02 112 m/z = 689.80 (C63H41N3 = 839.33) (C49H31N5 = 689.26) 113m/z = 689.80 114 m/z = 689.80 (C49H31N5 = 689.26) (C49H31N5 = 689.26)115 m/z = 687.83 116 m/z = 763.92 (C51H33N3 = 687.27) (C57H37N3 =763.30) 117 m/z = 840.02 118 m/z = 787.95 (C63H41N3 = 839.33) (C59H37N3= 787.30) 119 m/z = 737.89 120 m/z = 763.92 (C55H35N3 = 737.28)(C57H37N3 = 763.30) 121 m/z = 840.02 122 m/z = 689.80 (C63H41N3 =839.33) (C49H31N5 = 689.26) 123 m/z = 689.80 124 m/z = 689.80 (C49H31N5= 689.26) (C49H31N5 = 689.26) 125 m/z = 688.82 126 m/z = 764.91(C50H32N4 = 688.26) (C56H36N4 = 764.29) 127 m/z = 841.01 128 m/z =788.93 (C62H40N4 = 840.33) (C58H36N4 = 788.29) 129 m/z = 788.93 130 m/z= 764.91 (C58H36N4 = 788.29) (C56H36N4 = 764 .29) 131 m/z = 841.01 132m/z = 690.79 (C62H40N4 = 840.33) (C48H30N6 = 690.25) 133 m/z = 690.79134 m/z = 690.79 (C48H30N6 = 690.25) (C48H30N6 = 690.25) 135 m/z =688.82 136 m/z = 584.71 (C50H32N4 = 688.26) (C44H28N2 = 584.23) 137 m/z= 584.71 138 m/z = 584.71 (C44H28N2 = 584.23) (C44H28N2 = 584.23) 139m/z = 584.71 140 m/z = 584.71 (C44H28N2 = 584.23) (C44H28N2 = 584.23)141 m/z = 709.87 142 m/z = 759.93 (C55H35N = 709.28) (C59H37N = 759.29)143 m/z = 785.97 144 m/z = 886.09 (C61H39N = 785.31) (C69H43N = 885.34)145 m/z = 633.78 146 m/z = 657.74 (C49H31N = 633.25) (C47H32NOP =657.22) 147 m/z = 622.75 148 m/z = 698.85 (C47H30N2 = 622.24) (C53H34N2= 698.27) 149 m/z = 509.60 150 m/z = 585.69 (C37H23N3 = 509.19)(C43H27N3 = 585.22) 151 m/z = 509.60 152 m/z = 661.79 (C37H23N3 =509.19) (C49H31N3 = 661.25) 153 m/z = 561.67 154 m/z = 637.77 (C41H27N3= 561.22) (C47H31N3 = 637.25) 155 m/z = 713.87 156 m/z = 661.79(C53H35N3 = 713.28) (C49H31N3 = 661.25) 157 m/z = 661.79 158 m/z =637.77 (C49H31N3 = 661.25) (C47H31N3 = 637.25) 159 m/z = 713.87 160 m/z= 563.65 (C53H35N3 = 713.28) (C39H25N5 = 563.21) 161 m/z = 563.65 162m/z = 563.65 (C39H25N5 = 563.21) (C39H25N5 = 563.21) 163 m/z = 561.67164 m/z = 637.77 (C41H27N3 = 561.22) (C47H31N3 = 637.25) 165 m/z =713.87 166 m/z = 661.79 (C53H35N3 = 713.28) (C49H31N3 = 661.25) 167 m/z= 661.79 168 m/z = 637.77 (C49H31N3 = 661.25) (C47H31N3 = 637.25) 169m/z = 713.87 170 m/z = 563.65 (C53H35N3 = 713.28) (C39H25N5 = 563.21)171 m/z = 563.65 172 m/z = 563.65 (C39H25N5 = 563.21) (C39H25N5 =563.21) 173 m/z = 562.66 174 m/z = 638.76 (C40H26N4 = 562.22) (C46H30N4= 638.25) 175 m/z = 714.85 176 m/z = 662.78 (C52H34N4 = 714.28)(C48H30N4 = 662.25) 177 m/z = 662.78 178 m/z = 638.76 (C48H30N4 =662.25) (C46H30N4 = 638.25) 179 m/z = 714.85 180 m/z = 564.64 (C52H34N4= 714.28) (C38H24N6 = 564.21) 181 m/z = 564.64 182 m/z = 564.64(C38H24N6 = 564.21) (C38H24N6 = 564.21) 183 m/z = 562.66 184 m/z =458.55 (C40H26N4 = 562.22) (C34H22N2 = 458.18) 185 m/z = 458.55 186 m/z= 458.55 (C34H22N2 = 458.18) (C34H22N2 = 458.18) 187 m/z = 458.55 188m/z = 458.55 (C34H22N2 = 458.18) (C34H22N2 = 458.18) 189 m/z = 583.72190 m/z = 633.78 (C45H29N = 583.23) (C49H31N = 633.25) 191 m/z = 659.81192 m/z = 759.93 (C51H33N = 659.26) (C59H37N = 759.29) 193 m/z = 507.62194 m/z = 531.58 (C39H25N = 507.20) (C37H26NOP = 531.18) 195 m/z =496.60 196 m/z = 572.70 (C37H24N2 = 496.19) (C43H28N2 = 572.23) 197 m/z= 572.70 198 m/z = 737.89 (C43H28N2 = 572.23) (C55H35N3 = 737.28) 199m/z = 585.69 200 m/z = 661.79 (C43H27N3 = 585.22) (C49H31N3 = 661.25)201 m/z = 585.69 202 m/z = 737.89 (C43H27N3 = 585.22) (C55H35N3 =737.28) 203 m/z = 637.77 204 m/z = 713.87 (C47H31N3 = 637.25) (C53H35N3= 713.28) 205 m/z = 789.96 206 m/z = 737.89 (C59H39N3 = 789.31)(C55H35N3 = 737.28) 207 m/z = 737.89 208 m/z = 713.87 (C55H35N3 =737.28) (C53H35N3 = 713.28) 209 m/z = 789.96 210 m/z = 639.75 (C59H39N3= 789.31) (C45H29N5 = 639.24) 211 m/z = 639.75 212 m/z = 639.75(C45H29N5 = 639.24) (C45H29N5 = 639.24) 213 m/z = 637.77 214 m/z =713.87 (C47H31N3 = 637.25) (C53H35N3 = 713.28) 215 m/z = 789.96 216 m/z= 737.89 (C59H39N3 = 789.31) (C55H35N3 = 737.28) 217 m/z = 737.89 218m/z = 713.87 (C55H35N3 = 737.28) (C53H35N3 = 713.28) 219 m/z = 789.98220 m/z = 639.76 (C59H39N3 = 789.31) (C45H29N5 = 639.24) 221 m/z =639.76 222 m/z = 639.76 (C45H29N5 = 639.24) (C45H29N5 = 639.24) 223 m/z= 638.77 224 m/z = 714.87 (C46H30N4 = 638.24) (C52H34N4 = 714.27) 225m/z = 790.97 226 m/z = 738.89 (C58H38N4 = 790.31) (C54H34N4 = 738.27)227 m/z = 738.89 228 m/z = 714.87 (C54H34N4 = 738.27) (C52H34N4 =714.27) 229 m/z = 790.97(C58H38N4 = 790.31) 230 m/z = 640.75 (C44H28N6 =640.23) 231 m/z = 640.75 232 m/z = 640.75 (C44H28N6 = 640.23) (C44H28N6= 640.23) 233 m/z = 638.77 234 m/z = 534.66 (C46H30N4 = 638.24)(C40H26N2 = 534.21) 235 m/z = 534.66 236 m/z = 534.66 (C40H26N2 =534.21) (C = 40H26N2 = 534.21) 237 m/z = 534.66 238 m/z = 534.66(C40H26N2 = 534.21) (C40H26N2 = 534.21) 239 m/z = 659.83 240 m/z =709.89 (C51H33N = 659.26) (C55H35N = 709.27) 241 m/z = 735.93 242 m/z =836.05 (C57H37N = 735.29) (C65H41N = 835.32) 243 m/z = 583.73 244 m/z =607.69 (C45H29N = 583.23) (C43N30NOP = 607.20) 245 m/z = 572.71 246 m/z= 648.80 (C43H28N2 = 572.22) (C49H32N2 = 648.25) 247 m/z = 648.80 248m/z = 814.00 (C49H32N2 = 648.25) (C61H39N3 = 813.31) 249 m/z = 509.61250 m/z = 585.71 (C37H23N3 = 509.18) (C43H27N3 = 858.22) 251 m/z =509.61 252 m/z = 661.80 (C37H23N3 = 509.18) (C49H31N3 = 661.25) 253 m/z= 561.68 254 m/z = 637.78 (C41H27N3 = 561.22) (C47H31N3 = 637.25) 255m/z = 713.88 256 m/z = 661.80 (C53H35N3 = 713.28) (C49H31N3 = 661.25)257 m/z = 661.80 258 m/z = 637.78 (C49H31N3 = 661.25) (C47J31N3 =637.25) 259 m/z = 713.88 260 m/z = 563.66 (C53H35N3 = 713.28) (C39H25N5= 563.21) 261 m/z = 563.66 262 m/z = 563.66 (C39H25N5 = 563.21)(C39H25N5 = 563.21) 263 m/z = 561.68 264 m/z = 637.78 (C41H27N3 =561.22) (C47H31N3 = 637.25) 265 m/z = 713.88 266 m/z = 661.80 (C53H35N3= 713.28) (C49H31N3 = 661.25) 267 m/z = 661.80 268 m/z = 637.78(C49H31N3 = 661.25) (C47H31N3 = 637.25) 269 m/z = 713.88 270 m/z =563.66 (C53H35N3 = 713.28) (C39H25N5 = 563.21) 271 m/z = 563.66 272 m/z= 563.66 (C39H25N5 = 563.21) (C39H25N5 = 563.21) 273 m/z = 562.67 274m/z = 638.77 (C40H26N4 = 562.21) (C46H30N4 = 638.24) 275 m/z = 714.87276 m/z = 662.79 (C52H34N4 = 714.27) (C48H30N4 = 662.24) 277 m/z =662.79 278 m/z = 638.77 (C48H30N4 = 662.24) (C46H30N4 = 638.24) 279 m/z= 714.87 280 m/z = 564.65 (C52H34N4 = 714.27) (C38H24N6 = 564.20) 281m/z = 564.65 282 m/z = 564.65 (C38H24N6 = 564.20) (C38H24N6 = 564.20)283 m/z = 562.67 284 m/z = 458.56 (C40H26N4 = 562.21) (C34H22N2 =458.17) 285 m/z = 458.56 286 m/z = 458.56 (C34H22N2 = 458.17) (C34H22N2= 458.17) 287 m/z = 458.56 288 m/z = 458.56 (C34H22N2 = 458.17)(C34H22N2 = 458.17) 289 m/z = 583.73 290 m/z = 633.79 (C45H29N = 583.23)(C49H31N = 633.24) 291 m/z = 659.83 292 m/z = 759.95 (C51H33N = 659.26)(C59H37N = 759.29) 293 m/z = 507.63 294 m/z = 531.59 (C39H25N = 507.19)(C37H26NOP = 531.17) 295 m/z = 496.61 296 m/z = 572.71 (C37H24N2 =496.19) (C43H28N2 = 572.22) 297 m/z = 572.71 298 m/z = 737.90 (C43H28N2= 572.22) (C55H35N3 = 737.28) 299 m/z = 585.71 300 m/z = .661.80(C43H27N3 = 585.22) (C49H31N3 = 661.25) 301 m/z = 585.71 302 m/z =737.90 (C43H27N3 = 585.22) (C55H35N3 = 737.28) 303 m/z = 585.71 304 m/z= 737.90 (C43H27N3 = 585.22) (C55H35N3 = 737.28) 305 m/z = 637.78 306m/z = 713.88 (C47H31N3 = 637.25) (C53H35N3 = 713.28) 307 m/z = 789.98308 m/z = 737.90 (C59H39N3 = 789.31) (C55H35N3 = 737.28) 309 m/z =737.90 310 m/z = 713.88 (C55H35N3 = 737.28) (C53H35N3 = 713.28) 311 m/z= 789.98 312 m/z = 639.76 (C59H39N3 = 789.31) (C45H29N5 = 639.24) 313m/z = 639.76 314 m/z = 639.76 (C45H29N5 = 639.24) (C45H29N5 = 639.24)315 m/z = 637.78 316 m/z = 713.88 (C47H31N3 = 637.25) (C53H35N3 =713.28) 317 m/z = 789.98 318 m/z = 737.90 (C59H39N3 = 789.31) (C55H35N3= 737.28) 319 m/z = 737.90 320 m/z = 713.88 (C55H35N3 = 737.28)(C53H35N3 = 713.28) 321 m/z = 639.76 322 m/z = 639.76 (C45H29N5 =639.24) (C45H29N5 = 639.24) 323 m/z = 638.77 324 m/z = 714.87 (C46H30N4= 638.24) (C52H34N4 = 714.27) 325 m/z = 790.97 326 m/z = 738.89(C58H38N4 = 790.31) (C54H34N4 = 738.27) 327 m/z = 738.89 328 m/z =714.87 (C54H34N4 = 738.27) (C52H34N4 = 714.87) 329 m/z = 790.97 330 m/z= 640.75 (C58H38N4 = 790.31) (C44H28N6 = 640.23) 331 m/z = 640.75 332m/z = 640.75 (C44H28N6 = 640.23) (C44H28N6 = 640.23) 333 m/z = 638.77334 m/z = 534.66 (C46H30N4 = 638.24) (C40H26N2 = 534.21) 335 m/z =534.66 336 m/z = 534.66 (C44H26N2 = 534.21) (C40H26N2 = 534.21) 337 m/z= 534.66 338 m/z = 534.66 (C40H26N2 = 534.21) (C40H26N2 = 534.21) 339m/z = 659.83 340 m/z = 709.89 (C51H33N = 659.26) (C55H35N = 709.27) 341m/z = 735.93 342 m/z = 836.05 (C57H37N = 735.29) (C65H41N = 835.32) 343m/z = 583.73 344 m/z = 607.69 (C45H29N = 583.23) (C43H30NOP = 607.20)345 m/z = 572.71 346 m/z = 648.80 (C43H28N2 = 572.22) (C49H32N2 =648.25) 347 m/z = 648.80 348 m/z = 814.00 (C49H32N2 = 648.25) (C61H39N#= 813.31) 349 m/z = 635.77 350 m/z = 711.86 (C47H29N3 = 635.23)(C53H33N3 = 711.26) 351 m/z = 635.77 352 m/z = 787.96 (C47H29N3 =635.23) (C59H37N3 = 787.29) 353 m/z = 687.84 354 m/z = 763.94 (C51H33N3= 687.26) (C57H37N3 = 763.29) 355 m/z = 840.04 356 m/z = 787.96(C63H41N3 = 839.33) (C59H37N3 = 787.29) 357 m/z = 787.96 358 m/z =763.94 (C59H37N3 = 787.29) (C57H37N3 = 763.29) 359 m/z = 840.04 360 m/z= 689.82 (C63H41N3 = 839.33) (C49H31N5 = 689.25) 361 m/z = 689.82 362m/z = 689.82 (C49H31N5 = 689.25) (C49H31N5 = 689.25) 363 m/z = 687.84364 m/z = 763.94 (C51H33N3 = 687.26) (C57H37N4 = 763.29) 365 m/z =840.04 366 m/z = 787.96 (C63H41N3 = 839.33) (C59H3N3 = 787.29) 367 m/z =787.96 368 m/z = 763.94 (C59H37N3 = 787.29) (C57H37N3 = 763.29) 369 m/z= 840.04 370 m/z = 689.82 (C63H41N3 = 839.33) 372 (C49H31N5 = 689.25)371 m/z = 689.82 m/z = 689.82 (C49H31N5 = 689.25) 374 (C49H31N5 =689.25) 373 m/z = 688.83 374 m/z = 764.93 (C50H32N4 = 688.26) (C56H36N4= 764.29) 375 m/z = 841.03 376 m/z = 788.95 (C62H40N4 = 840.32)(C58H36N4 = 788.29) 377 m/z = 788.95 378 m/z = 764.93 (C58H36N4 =788.29) (C56H36N4 = 764.29) 379 m/z = 841.03 380 m/z = 690.81 (C62H40N4= 840.32) (C48H30N6 = 690.25) 381 m/z = 690.81 382 m/z = 690.81(C48H30N6 = 690.25) (C48H30N6 = 690.25) 383 m/z = 688.83 384 m/z =584.72 (C50H32N4 = 688.26) (C44H28N2 = 584.22) 385 m/z = 584.72 386 m/z= 584.72 (C44H28N2 = 584.22) (C44H28N2 = 584.22) 387 m/z = 584.72 388m/z = 584.72 (C44H28N2 = 584.22) (C44H28N2 = 584.22) 389 m/z = 709.89390 m/z = 759.95 (C55H35N = 709.27) (C59H37N = 759.29) 391 m/z = 785.99392 m/z = 886.11 (C61H39N = 785.30) (C69H43N = 885.34) 393 m/z = 633.79394 m/z = 657.75 (C49H31N = 633.24) (C47H32NOP = 657.22) 395 m/z =622.77 396 m/z = 698.86 (C47H30N2 = 622.24) (C53H34N2 = 698.27) 397 m/z= 698.86 398 m/z = 864.06 (C53H34N2 = 698.27) (C65.41N3 = 863.33) 399m/z = 509..61 400 m/z = 585.71 (C37H23N3 = 509.18) (C43H27N3 = 585.22)401 m/z = 509.61 402 m/z = 661.80 (C37H23N3 = 509.18) (C49H31N3 =661.25) 403 m/z = 561.68 404 m/z = 637.78 (C41H27N3 = 561.22) (C47H31N3= 637.25) 405 m/z = 713.88 406 m/z = 661.80 (C53H35N3 = 713.28)(C49H31N3 = 661.25) 407 m/z = 661.80 408 m/z = 637.78 (C49H31N3 =661.25) (C47H31N3 = 637.25) 409 m/z = 713.88 410 m/z = 563.66 (C53N35N3= 713.28) (C39H25N5 = 563.21) 411 m/z = 563.66 412 m/z = 563.66(C39H25N5 = 563.21) (C39H25N5 = 563.21) 413 m/z = 561.68 414 m/z =637.78 (C41H27N3 = 561.22) (C47H31N3 = 637.25) 415 m/z = 713.88 416 m/z= 661.80 (C53H35N3 = 713.28) (C49H31N3 = 661.25) 417 m/z = 661.80 418m/z = 637.78 (C49H31N3 = 661.25) (C47H31N3 = 637.25) 419 m/z = 713.88420 m/z = 563.66 (C53H35N3 = 713.28) (C39H25N5 = 563.21) 421 m/z =563.66 422 m/z = 563.66 (C39H25N5 = 563.21) (C39H25N5 = 563.21) 423 m/z= 562.67 424 m/z = 638.77 (C40H26N4 = 562.21) (C46H30N4 = 638.24) 425m/z = 714.87 426 m/z = 662.79 (C52H34N4 = 714.27) (C48H30N4 = 662.24)427 m/z = 662.79 428 m/z = 638.77 (C48H30N4 = 662.24) (C46H30N4 =638.24) 429 m/z = 714.87 430 m/z = 564.65 (C52H34N4 = 714.27) (C38N24N6= 564.20) 431 m/z = 564.65 432 m/z = 564.65 (C38H24N6 = 564.20)(C38H24N6 = 564.20) 433 m/z = 562.67 434 m/z = 458.56 (C40H26N4 =562.21) (C34H22N2 = 458.17) 435 m/z = 458.56 436 m/z = 458.56 (C34H22N2= 458.17) (C34H22N2 = 458.17) 437 m/z = 458.56 438 m/z = 458.56(C34H22N2 = 458.17) (C34H22N2 = 458.17) 439 m/z = 583.73 440 m/z =633.79 (C45H29N = 583.23) (C49H31N = 633.24) 441 m/z = 659.83 442 m/z =759.95 (C51H33N = 659.26) (C59H37N = 859.29) 443 m/z = 507.63 444 m/z =531.59 (C39H25N = 507.19) (C37H26NOP = 531.17) 445 m/z = 496.61 446 m/z= 572.71 (C37H24N2 = 496.19) (C43H28N2 = 572.22) 447 m/z = 572.71 448m/z = 737.90 (C43H28N2 = 572.22) (C55H35N3 = 737.28) 449 m/z = 585.71450 m/z = 661.80 (C43H27N3 = 585.22) (C49H31N3 = 661.25) 451 m/z =585.71 452 m/z = 737.90 (C43H27N3 = 585.22) (C55H35N3 = 737.28) 453 m/z= 637.78 454 m/z = 713.88 (C47H31N3 = 637.25) (C55H35N3 = 713.28) 455m/z = 789.98 456 m/z = 737.90 (C59H39N3 = 789.31) (C55H35N3 = 737.28)457 m/z = 737.90 458 m/z = 713.88 (C55H35N3 = 737.28) (C53H35N3 =714.28) 459 m/z = 789.98 460 m/z = 639.76 (C59H39N3 = 789.31) (C45H29N5= 639.24) 461 m/z = 639.76 462 m/z = 639.76 (C45H29N5 = 639.24)(C45H29N5 = 639.24) 463 m/z = 637.78 464 m/z = 713.88 (C47H31N3 =637.25) (C53H35N3 = 713.28) 465 m/z = 789.98 466 m/z = 737.90 (C59H39N3= 789.31) (C55H35N3 = 737.28) 467 m/z = 737.90 468 m/z = 713.88(C55H35N3 = 737.28) (C53H35N3 = 713.28) 469 m/z = 789.98 470 m/z =639.76 (C59H39N3 = 789.31) (C45H29N5 = 639.24) 471 m/z = 639.76 472 m/z= 639.76 (C45H29N5 = 639.24) (C45H29N5 = 639.24) 473 m/z = 683.77 474m/z = 714.87 (C46H30N4 = 638.24) (C52H34N4 = 714.27) 475 m/z = 790.97476 m/z = 738.89 (C58H36N4 = 790.31) (C54H34N4 = 738.27) 477 m/z =738.89 478 m/z = 714.87 (C54H34N4 = 738.27) (C52H34N4 = 714.27) 479 m/z= 790.97 480 m/z = 640.75 (C58H38N4 = 790.31) (C44H28N6 = 640.23) 481m/z = 640.75 482 m/z = 640.75 (C44H28N6 = 640.23) (C44H28N6 = 640.23)483 m/z = 638.77 484 m/z = 534.66 (C46H30N4 = 638.24) (C40H26N2 =534.21) 485 m/z = 534.66 486 m/z = 534.66 (C40H26N2 = 534.21) (C40H26N2= 534.21) 487 m/z = 534.66 488 m/z = 534.66 (C40H26N2 = 534.21)(C40H26N2 = 534.21) 489 m/z = 659.83 490 m/z = 709.86 (C51H33N = 659.26)(C55H35N = 709.27) 491 m/z = 735.93 492 m/z = 836.05 (C57H37N = 735.29)(C65H41N = 835.32) 493 m/z = 583.73 494 m/z = 608.69 (C45H29N = 583.23)(C43H30NOP = 607.20) 495 m/z = 572.71 496 m/z = 648.80 (C43H28N2 =572.22) (C49H32N2 = 648.25) 497 m/z = 648.80 498 m/z = 814.00 (C49H32N2= 648.25) (C61H39N3 = 813.31) 499 m/z = 635.77 500 m/z = 711.86(C47H29N3 = 635.23) (C53H33N3 = 711.26) 501 m/z = 635.77 502 m/z =787.96 (C47H29N3 = 635.23) (C59H37N3 = 787.29) 503 m/z = 687.84 504 m/z= 763.94 (C51H33N3 = 687.26) (C57H37N3 = 763.29) 505 m/z = 840.04 506m/z = 787.96 (C63H41N3 = 839.33) (C59H37N3 = 787.29) 507 m/z = 787.96508 m/z = 763.94 (C59H37N3 = 787.29) (C57H37N3 = 763.29) 509 m/z =840.04 510 m/z = 689.82 (C63H41N3 = 839.33) (C49H31N5 = 689.25) 511 m/z= 689.82 512 m/z = 689.82 (C49H31N5 = 689.25) (C49H31N5 = 689.25) 513m/z = 687.84 514 m/z = 763.94 (C51H33N3 = 687.26) (C57H37N3 = 763.29)515 m/z = 840.04 516 m/z = 787.96 (C63H41N3 = 839.33) (C59H37N3 =787.29) 517 m/z = 787.96 518 m/z = 763.94 (C59H37N3 = 787.29) (C57H37N3= 763.29) 519 m/z = 840.04 520 m/z = 689.82 (C63H41N3 = 839.33)(C49H31N5 = 689.25) 521 m/z = 689.82 522 m/z = 689.82 (C49H31N5 =689.25) (C49H31N5 = 689.25) 523 m/z = 688.83 524 m/z = 764.93 (C50H32N4= 688.26) (C56H36N4 = 764.29) 525 m/z = 841.03 526 m/z = 788.95(C62H40N4 = 840.32) (C58H36N4 = 788.29) 527 m/z = 788.95 528 m/z =764.93 (C58H36N4 = 788.29) (C56H36N4 = 764.29) 529 m/z = 841.03 530 m/z= 690.81 (C62H40N4 = 840.32) (C48H30N6 = 690.25) 531 m/z = 690.81 532m/z = 690.81 (C48H30N6 = 690.25) (C48H30N6 = 690.25) 533 m/z = 688.83534 m/z = 584.72 (C50H32N4 = 688.26) (C44H28N2 = 584.22) 535 m/z =584.72 536 m/z = 584.72 (C44H28N2 = 584.22) (C44H28N2 = 584.22) 537 m/z= 584.72 538 m/z = 584.72 (C44H28N2 = 584.22) (C44H28N2 = 584.22) 539m/z = 709.89 540 m/z = 759.95 (C55H35N = 709.27) (C59H37N = 759.29) 541m/z = 673.85 542 m/z = 657.75 (C52H35N = 673.27) (C47H32NOP = 657.22)543 m/z = 622.77 544 m/z = 698.86 (C44H30N2 = 622.24) (C53H34N2 =698.27) 545 m/z = 698.86 546 m/z = 865.06 (C53H34N2 = 698.27) (C65H41N3= 863.33) 547 m/z = 661.80 548 m/z = 661.80 (C49H31N3 = 661.25)(C49H31N3 = 661.25) 549 m/z = 791.95 550 m/z = 791.95 (C57H37N5 =791.30) (C57H37N5 = 791.30) 551 m/z = 791.95 552 m/z = 791.95 (C57H37N5= 791.30) (C57H37N5 = 791.30) 553 m/z = 793.93 554 m/z = 793.93(C55H35N7 = 793.29) (C55H35N7 = 793.29) 555 m/z = 711.02 556 m/z =659.01 (C53H33N3 = 711.27) (C51H33N = 659.26) 557 m/z = 659.02 558 m/z =662.96 (C51H33N = 659.26) (C49H28NO2 = 663.22) 559 m/z = 659.12 560 m/z= 662.19 (C49H29NS2 = 659.17) (C49H30N2O = 662.24) 561 m/z = 678.17 562m/z = 662.19 (C49H30N2S = 678.21) (C49H30N2O = 662.24) 563 m/z = 662.19564 m/z = 728.21 (C49H30N2O = 662.24) (C52H32N4O = 728.26) 565 m/z =744.18 566 m/z = 728.21 (C52H32N4S = 774.23) (C52H32N4O = 728.26) 567m/z = 662.19 568 m/z = 804.23 (C49H30N2O = 662.24) (C58H36N4O = 804.29)569 m/z = 803.24 570 m/z = 803.23 (C59H37N3O = 803.29) (C59H37N3O =803.29) 571 m/z = 678.16 572 m/z = 727.20 (C49H30N2S = 678.21)(C53H33N3O = 727.26) 573 m/z = 727.19 574 m/z = 662.19 (C53H33N3O =727.26) (C49H30N2O = 662.24) 575 m/z = 662.20 576 m/z = 659.21(C49H30N2O = 662.24) (C51H33N = 659.26) 577 m/z = 659.20 578 m/z =663.17 (C51H33N = 659.26) (C49H29NO2 = 663.22) 579 m/z = 695.12 580 m/z= 728.22 (C49H29NS2 = 695.17) (C52H32N4O = 728.26) 581 m/z = 744.18 582m/z = 728.20 (C52H32N4S = 744.23) (C52H32N4O = 728.26) 583 m/z = 728.21584 m/z = 804.23 (C52H32N4O = 728.26) (C58H36N4O = 804.29) 585 m/z =820.22 586 m/z = 728.21 (C58H36N4S = 820.27) (C52H36N4O = 728.26) 587m/z = 804.21 588 m/z = 804.22 (C58H36N4O = 804.29) (C58H36N4O = 804.29)589 m/z = 803.23 590 m/z = 819.21 (C59H37N3O = 803.29) (C59H37N3S =819.27) 591 m/z = 803.22 592 m/z = 727.21 (C59H37N3O = 803.29)(C53H33N3O = 727.26) 593 m/z = 727.21 594 m/z = 727.22 (C53H33N3O =727.26) (C53H33N3O = 727.26) 595 m/z = 727.22 (C53H33N3O = 727.26)

EXPERIMENTAL EXAMPLE Experimental Example 1

1) Manufacture of Organic Light Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water and ultrasonic waves. Afterthe cleaning with distilled water was finished, the substrate wasultrasonic cleaned with solvents such as acetone, methanol and isopropylalcohol, then dried, and UVO treatment was carried out for 5 minutes ina UV cleaner using UV. After that, the substrate was transferred to aplasma cleaner (PT), and plasma treatment was carried out under vacuumfor removing ITO work function and remaining film, and the substrate wastransferred to a thermal deposition apparatus for organic deposition.

On the ITO transparent electrode (anode), organic materials were formedin a two-stack white organic light emitting diode (WOLED) structure. Asfor the first stack, a M hole transfer layer was formed first by thermalvacuum depositing TAPC to a thickness of 300 Å. After forming the holetransfer layer, a light emitting layer was thermal vacuum depositedthereon as follows. The light emitting layer was deposited to 300 Å bydoping Flrpic in 8% as a blue phosphorescent dopant to TCzl, a host. Anelectron transfer layer was formed to 400 Å using TmPyPB, and then acharge generation layer was formed to 100 Å by doping Cs₂CO₃ in 20% to acompound described in the following Table 6.

As for the second stack, a hole injection layer was formed first bythermal vacuum depositing MoO₃ to a thickness of 50 Å. A hole transferlayer, a common layer, was formed by doping MoO₃ to TAPC in 20% andforming to 100 Å, and then depositing TAPC to 300 Å. After depositing alight emitting layer to 300 Å thereon by doping Ir(ppy), a greenphosphorescent dopant, in 8% to TCzl, a host, an electron transfer layerwas formed to 600 Å using TmPyPB. Lastly, an electron injection layerwas formed on the electron transfer layer by depositing lithium fluoride(LiF) to a thickness of 10 Å, and then a cathode was formed on theelectron injection layer by depositing an aluminum (Al) cathode to athickness of 1,200 Å to manufacture an organic light emitting device.

Meanwhile, all the organic compounds required to manufacture the OLEDdevice were vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr byeach material to be used in the OLED manufacture.

2) Driving Voltage and Light Emission Efficiency of Organic LightEmitting Device

For the organic light emitting devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T95 when standard luminance was 3,500 cd/m² was measured usinga lifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organic lightemitting devices manufactured according to the present disclosure are asshown in Table 6.

TABLE 6 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 1  1 7.13 69.21 (0.221, 0.434) 42Example 2  2 7.01 69.82 (0.220, 0.440) 43 Example 3  3 7.10 69.45(0.219, 0.429) 41 Example 4  5 7.78 59.95 (0.218, 0.427) 27 Example 5 15 7.95 59.45 (0.220, 0.431) 28 Example 6  25 7.92 59.88 (0.200, 0.421)29 Example 7  35 7.17 66.23 (0.205, 0.411) 49 Example 8  36 7.60 63.89(0.204, 0.413) 36 Example 9  44 7.55 62.77 (0.210, 0.410) 38 Example 1045 7.34 67.70 (0.208, 0.420) 35 Example 11 46 7.74 58.52 (0.212, 0.428)29 Example 12 47 7.81 59.50 (0.223, 0.415) 32 Example 13 48 7.72 58.81(0.219, 0.410) 34 Example 14 50 7.79 63.08 (0.212, 0.429) 30 Example 1551 7.60 62.00 (0.213, 0.420) 31 Example 16 52 7.02 69.78 (0.223, 0.433)41 Example 17 75 7.89 58.98 (0.219, 0.411) 35 Example 18 85 7.80 59.11(0.210, 0.412) 35 Example 19 86 7.65 58.54 (0.211, 0.415) 39 Example 2094 7.56 59.06 (0.214, 0.420) 33 Example 21 95 7.80 54.22 (0.215, 0.411)36 Example 22 96 7.49 57.94 (0.211, 0.419) 37 Example 23 97 7.66 58.26(0.209, 0.419) 31 Example 24 98 7.58 59.11 (0.207, 0.409) 38 Example 25100 7.50 56.66 (0.208, 0.415) 35 Example 26 102 7.21 69.56 (0.224,0.429) 40 Example 27 149 7.07 70.01 (0.225, 0.429) 42 Example 28 1507.12 67.56 (0.209, 0.415) 44 Example 29 151 7.00 69.89 (0.231, 0.440) 42Example 30 153 7.05 69.47 (0.222, 0.435) 41 Example 31 163 7.87 65.84(0.218, 0.421) 30 Example 32 173 7.63 64.96 (0.220, 0.421) 28 Example 33183 7.37 67.13 (0.221, 0.433) 47 Example 34 192 7.55 59.99 (0.215,0.422) 40 Example 35 193 7.80 57.11 (0.214, 0.420) 39 Example 36 1948.00 59.21 (0.209, 0.432) 26 Example 37 195 7.44 57.84 (0.210, 0.430) 29Example 38 196 7.54 58.22 (0.211, 0.428) 30 Example 39 198 7.74 67.32(0.230, 0.439) 32 Example 40 199 7.08 69.74 (0.243, 0.442) 43 Example 41200 7.60 59.08 (0.231, 0.430) 39 Example 42 242 7.58 55.11 (0.228,0.428) 31 Example 43 243 7.70 54.01 (0.210, 0.430) 34 Example 44 2447.49 55.90 (0.219, 0.422) 34 Example 45 245 7.66 56.10 (0.229, 0.419) 38Example 46 246 7.88 57.04 (0.231, 0.418) 37 Example 47 248 7.85 55.28(0.227, 0.419) 37 Example 48 249 7.11 65.55 (0.243, 0.442) 39 Example 49250 7.34 61.00 (0.234, 0.439) 36 Example 50 253 7.45 59.80 (0.231,0.423) 39 Example 51 263 7.44 57.20 (0.234, 0.433) 39 Example 52 2737.60 57.98 (0.230, 0.421) 35 Example 53 292 7.51 52.17 (0.228, 0.418) 33Example 54 293 7.49 53.66 (0.228, 0.418) 38 Example 55 294 7.55 53.90(0.230, 0.420) 33 Example 56 295 7.52 52.10 (0.230, 0.424) 35 Example 57296 7.49 53.82 (0.231, 0.425) 34 Example 58 298 7.60 55.16 (0.232,0.425) 34 Example 59 299 7.72 54.67 (0.233, 0.419) 30 Example 60 3007.66 54.90 (0.232, 0.421) 39 Example 61 301 7.56 55.10 (0.238, 0.423) 38Example 62 303 7.60 56.22 (0.238, 0.421) 38 Example 63 313 7.55 56.88(0.239, 0.422) 36 Example 64 323 7.47 57.10 (0.231, 0.423) 39 Example 65333 7.51 56.12 (0.232, 0.431) 34 Example 66 342 7.41 59.99 (0.233,0.433) 31 Example 67 343 7.44 58.89 (0.238, 0.438) 33 Example 68 3447.39 63.38 (0.243, 0.442) 40 Example 69 345 7.22 66.22 (0.243, 0.442) 32Example 70 346 7.66 59.80 (0.231, 0.423) 36 Example 71 348 7.55 59.10(0.238, 0.423) 37 Example 72 399 7.80 55.88 (0.209, 0.419) 37 Example 73400 7.79 56.18 (0.210, 0.420) 35 Example 74 401 7.65 55.97 (0.211,0.421) 38 Example 75 403 7.45 56.45 (0.212, 0.422) 38 Example 76 4137.49 55.10 (0.228, 0.418) 38 Example 77 423 7.54 56.89 (0.231, 0.420) 36Example 78 442 7.49 56.25 (0.233, 0.419) 35 Example 79 443 7.80 56.25(0.229, 0.423) 35 Example 80 444 7.77 56.67 (0.230, 0.421) 38 Example 81445 7.69 54.20 (0.231, 0.419) 33 Example 82 446 7.64 55.11 (0.230,0.423) 34 Example 83 448 7.65 53.10 (0.231, 0.422) 35 Example 84 4497.76 53.88 (0.229. 0.424) 35 Example 85 450 7.68 54.10 (0.230, 0.424) 38Example 86 451 7.70 56.34 (0.233, 0.419) 38 Example 87 453 7.75 56.38(0.231, 0.420) 39 Example 88 463 7.68 57.20 (0.233, 0.421) 35 Example 89473 7.71 57.11 (0.232, 0.422) 33 Example 90 484 7.72 55.55 (0.232,0.421) 32 Example 91 492 7.76 55.40 (0.232, 0.422) 32 Example 92 4937.66 56.10 (0.230, 0.420) 33 Example 93 494 7.56 56.88 (0.231, 0.419) 35Example 94 495 7.60 56.80 (0.229, 0.423) 36 Example 95 496 7.58 56.15(0.228, 0.424) 37 Example 96 498 7.49 56.87 (0.226, 0.434) 37 Example 97499 7.48 55.87 (0.228, 0.429) 38 Example 98 500 7.51 54.99 (0.229,0.430) 30 Example 99 555 7.02 68.99 (0.228, 0.436) 41 Example 100 5567.44 67.21 (0.243, 0.442) 38 Comparative TmPyPB 8.57 57.61 (0.212,0.433) 24 Example 1-1 Comparative BBQB 8.43 58.11 (0.220, 0.429) 27Example 1-2 Comparative TBQB 8.47 58.90 (0.222, 0.430) 28 Example 1-3

As shown from the results of Table 6, the organic light emitting devicesusing the charge generation layer material of the 2-stack white organiclight emitting device of the present disclosure had a low drivingvoltage and improved light emission efficiency compared to ComparativeExample 1. Particularly, it was identified that Compounds 1, 2, 3, 35,52, 102, 149, 150, 151, 183, 199 and 555 were significantly excellent inall of driving, efficiency and lifespan.

The presumed reason for such results is that the compound of the presentdisclosure used as an N-type charge generation layer formed with aninvented skeleton having proper length, strength and flat property and aproper hetero-compound capable of binding with metals is doped with analkali metal or an alkali-earth metal to form a gap state within theN-type charge generation layer, and electrons produced from a P-typecharge generation layer are readily injected to the electron transferlayer through the gap state produced within the N-type charge generationlayer. Accordingly, the P-type charge generation layer favorably carriedout electron injection and electron transfer to the N-type chargegeneration layer, and as a result, it is considered that a drivingvoltage of the organic light emitting device decreased, and efficiencyand lifespan were improved.

Experimental Example 2

1) Manufacture of Organic Light Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water and ultrasonic waves. Afterthe cleaning with distilled water was finished, the substrate wasultrasonic cleaned with solvents such as acetone, methanol and isopropylalcohol, then dried, and UVO treatment was carried out for 5 minutes ina UV cleaner using UV. After that, the substrate was transferred to aplasma cleaner (PT), and plasma treatment was carried out under vacuumfor removing ITO work function and remaining film, and the substrate wastransferred to a thermal deposition apparatus for organic deposition. Onthe ITO transparent electrode (anode), organic materials were formed ina single-stack structure. As a hole injection layer, HAT-CN wasdeposited to a thickness of 50 Å, and subsequently, a hole transferlayer was formed by doping DNTPD within 10% to NPD, depositing theresult to a thickness of 1500 Å, and continuously depositing TCTA to athickness of 200 Å. Subsequently, a light emitting layer comprising at-Bu-perylene dopant in an ADN host was formed to a thickness of 250 Å.Next, Alq₃, an electron transfer layer, was formed to a thickness of 250Å, and an N-type charge transfer layer was formed to a thickness of 100Å by doping Li, an alkali metal, to a compound described in thefollowing Table 7, and Al, a cathode, was formed to a thickness ofapproximately 1,000 Å to manufacture an organic light emitting device.

2) Driving Voltage and Light Emission Efficiency of Organic LightEmitting Device

For the organic light emitting devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T₉₅ when standard luminance was 750 cd/m² was measured using alifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organicelectroluminescent devices manufactured according to the presentdisclosure are as shown in Table 7.

TABLE 7 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 101 1 4.49 6.91 (0.134, 0.101) 40Example 102 2 4.50 6.92 (0.134, 0.101) 41 Example 103 3 4.50 6.93(0.134, 0.100) 42 Example 104 5 4.92 6.21 (0.134, 0.105) 30 Example 10515 4.86 6.20 (0.134, 0.105) 29 Example 106 25 4.95 6.22 (0.134, 0.104)31 Example 107 35 4.61 6.69 (0.134, 0.099) 47 Example 108 36 4.97 6.15(0.134, 0.103) 35 Example 109 44 4.98 6.21 (0.134, 0.102) 34 Example 11045 4.80 6.10 (0.134, 0.101) 40 Example 111 46 5.50 6.33 (0.134, 0.101)41 Example 112 47 5.20 6.29 (0.134, 0.103) 32 Example 113 48 5.14 6.18(0.134, 0.102) 34 Example 114 50 5.02 6.51 (0.134, 0.101) 31 Example 11551 5.05 6.27 (0.134, 0.104) 33 Example 116 52 4.62 6.91 (0.134, 0.101)39 Example 117 75 5.11 6.44 (0.134, 0.104) 35 Example 118 85 5.21 6.47(0.134, 0.103) 34 Example 119 86 5.29 6.32 (0.134, 0.102) 35 Example 12094 5.20 6.33 (0.134, 0.102) 33 Example 121 95 5.25 6.27 (0.134, 0.104)33 Example 122 96 5.18 6.29 (0.134, 0.104) 34 Example 123 97 5.09 6.31(0.134, 0.102) 37 Example 124 98 5.04 6.14 (0.134, 0.104) 36 Example 125100 5.09 6.22 (0.134, 0.101) 37 Example 126 102 4.46 6.84 (0.134, 0.102)41 Example 127 149 4.56 6.90 (0.134, 0.101) 40 Example 128 150 4.51 6.94(0.134, 0.101) 40 Example 129 151 4.55 6.94 (0.134, 0.100) 42 Example130 153 4.60 6.98 (0.134, 0.099) 42 Example 131 163 5.65 6.22 (0.134,0.104) 34 Example 132 173 5.68 6.15 (0.134, 0.104) 33 Example 133 1835.82 6.45 (0.134, 0.105) 30 Example 134 192 5.50 6.45 (0.134, 0.102) 31Example 135 193 5.44 6.54 (0.134, 0.103) 32 Example 136 194 5.80 6.62(0.134, 0.101) 29 Example 137 195 5.60 6.59 (0.134, 0.102) 30 Example138 196 5.49 6.50 (0.134, 0.103) 31 Example 139 198 5.77 6.43 (0.134,0.101) 30 Example 140 199 4.40 6.98 (0.134, 0.099) 40 Example 141 2005.21 6.44 (0.134, 0.101) 35 Example 142 242 5.44 6.43 (0.134, 0.103) 34Example 143 243 5.45 6.30 (0.134, 0.102) 34 Example 144 244 5.55 6.29(0.134, 0.103) 32 Example 145 245 5.56 6.34 (0.134, 0.102) 31 Example146 246 5.46 6.38 (0.134, 0.103) 33 Example 147 248 5.55 6.40 (0.134,0.101) 30 Example 148 249 4.99 6.34 (0.134, 0.100) 32 Example 149 2505.40 6.35 (0.134, 0.102) 33 Example 150 253 5.44 6.40 (0.134, 0.101) 34Example 151 263 5.50 6.41 (0.134, 0.102) 35 Example 152 273 5.34 6.38(0.134, 0.101) 33 Example 153 292 5.33 6.39 (0.134, 0.103) 32 Example154 293 5.45 6.40 (0.134, 0.101) 33 Example 155 294 5.44 6.42 (0.134,0.103) 31 Example 156 295 5.34 6.44 (0.134, 0.104) 30 Example 157 2965.41 6.20 (0.134, 0.103) 30 Example 158 298 5.39 6.38 (0.134, 0.101) 33Example 159 299 5.37 6.30 (0.134, 0.103) 32 Example 160 300 5.35 6.29(0.134, 0.103) 32 Example 161 301 5.45 6.40 (0.134, 0.101) 33 Example162 303 5.51 6.33 (0.134, 0.102) 31 Example 163 313 5.20 6.26 (0.134,0.102) 34 Example 164 323 5.33 6.24 (0.134, 0.101) 33 Example 165 3335.30 6.30 (0.134, 0.101) 33 Example 166 342 5.20 6.34 (0.134, 0.101) 31Example 167 343 5.25 6.37 (0.134, 0.102) 31 Example 168 344 5.10 6.62(0.134, 0.101) 34 Example 169 345 5.00 6.28 (0.134, 0.100) 39 Example170 346 5.35 6.30 (0.134, 0.102) 35 Example 171 348 5.33 6.32 (0.134,0.103) 34 Example 172 399 5.44 6.20 (0.134, 0.104) 37 Example 173 4005.39 6.35 (0.134, 0.101) 35 Example 174 401 5.44 6.33 (0.134, 0.101) 33Example 175 403 5.45 6.32 (0.134, 0.104) 35 Example 176 413 5.46 6.35(0.134, 0.103) 34 Example 177 423 5.48 6.21 (0.134, 0.103) 37 Example178 442 5.44 6.33 (0.134, 0.102) 36 Example 179 443 5.44 6.38 (0.134,0.102) 36 Example 180 444 5.41 6.20 (0.134, 0.101) 31 Example 181 4455.44 6.22 (0.134, 0.101) 32 Example 182 446 5.50 6.34 (0.134, 0.100) 32Example 183 448 5.49 6.21 (0.134, 0.104) 34 Example 184 449 5.48 6.24(0.134, 0.103) 32 Example 185 450 5.47 6.22 (0.134, 0.104) 32 Example186 451 5.43 6.38 (0.134, 0.103) 36 Example 187 453 5.42 6.23 (0.134,0.102) 34 Example 188 463 5.46 6.29 (0.134, 0.102) 34 Example 189 4735.44 6.30 (0.134, 0.101) 35 Example 190 484 5.41 6.22 (0.134, 0.101) 35Example 191 492 5.36 6.34 (0.134, 0.103) 37 Example 192 493 5.45 6.31(0.134, 0.102) 34 Example 193 494 5.50 6.33 (0.134, 0.102) 33 Example194 495 5.49 6.25 (0.134, 0.101) 32 Example 195 496 5.48 6.22 (0.134,0.101) 35 Example 196 498 5.55 6.34 (0.134, 0.103) 36 Example 197 4995.49 6.35 (0.134, 0.104) 34 Example 198 500 5.42 6.30 (0.134, 0.103) 33Example 199 555 4.55 6.93 (0.134, 0.100) 41 Example 200 556 4.79 6.44(0.134, 0.102) 35 Comparative Bphen 5.82 6.23 (0.134, 0.110) 27 Example2-1 Comparative BBQB 5.80 6.32 (0.134, 0.111) 29 Example 2-2 ComparativeTBQB 5.84 6.39 (0.134, 0.111) 25 Example 2-3

As shown from the results of Table 7, the organic light emitting devicesusing the charge generation layer material of the blue organic lightemitting device of the present disclosure had a low driving voltage andimproved light emission efficiency compared to Comparative Example 2.Particularly, it was identified that Compounds 1, 2, 3, 35, 52, 102,149, 150, 151, 183, 199 and 555 were significantly excellent in all ofdriving, efficiency and lifespan.

The presumed reason for such results is that the compound of the presentdisclosure used as an N-type charge generation layer formed with aninvented skeleton having proper length, strength and flat property and aproper hetero-compound capable of binding with metals is doped with analkali metal or an alkali-earth metal to form a gap state within theN-type charge generation layer, and electrons produced from a P-typecharge generation layer are readily injected to the electron transferlayer through the gap state produced within the N-type charge generationlayer. Accordingly, the P-type charge generation layer favorably carriedout electron injection and electron transfer to the N-type chargegeneration layer, and as a result, it is considered that a drivingvoltage of the organic light emitting device decreased, and efficiencyand lifespan were improved.

Experimental Example 3

1) Manufacture of Organic Light Emitting Device

A transparent electrode ITO thin film obtained from glass for an OLED(manufactured by Samsung Corning Advanced Glass) was ultrasonic cleanedconsecutively using trichloroethylene, acetone, ethanol and distilledwater for 5 minutes each, placed in isopropanol and stored, and thenused.

Next, the ITO substrate was installed in a substrate folder of vacuumdeposition equipment, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) wasintroduced to a cell in the vacuum deposition equipment.

Subsequently, the chamber was exhausted until the degree of vacuuminside the chamber reached 10⁻⁶ torr, and then a current was applied tothe cell to evaporate the 2-TNATA to deposit a hole injection layerhaving a thickness of 600 Å on the ITO substrate.

The following N,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) wasintroduced to a different cell in the vacuum deposition equipment, acurrent was applied to the cell to evaporate to deposit a hole transferlayer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as follows wasdeposited thereon as a light emitting layer. Specifically, H1, a bluelight emitting host material, was vacuum deposited to a thickness of 200Å on one cell in the vacuum deposition equipment, and D1, a blue lightemitting dopant material, was vacuum deposited thereon in 5% withrespect to the host material.

Subsequently, a compound of the following structural formula E1 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was formed to a thickness of1,000 Å to manufacture an OLED device.

Meanwhile, all the organic compounds required to manufacture the OLEDdevice were vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr byeach material to be used in the OLED manufacture.

2) Driving Voltage and Light Emission Efficiency of Organic LightEmitting Device

For the organic light emitting devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T₉₅ when standard luminance was 700 cd/m² was measured using alifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organic lightemitting devices manufactured according to the present disclosure are asshown in Table 8.

TABLE 8 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 201 1 5.48 6.02 (0.134, 0.102) 32Example 202 2 5.39 6.24 (0.134, 0.102) 31 Example 203 3 5.35 6.34(0.134, 0.100) 31 Example 204 5 4.45 6.98 (0.134, 0.100) 40 Example 20515 4.50 6.99 (0.134, 0.101) 41 Example 206 25 4.48 6.85 (0.134, 0.099)40 Example 207 35 5.38 5.64 (0.134, 0.100) 29 Example 208 36 5.44 5.85(0.134, 0.100) 33 Example 209 44 5.38 5.90 (0.134, 0.100) 36 Example 21045 5.22 6.01 (0.134, 0.100) 28 Example 211 46 4.70 6.67 (0.134, 0.102)61 Example 212 47 5.28 6.10 (0.134, 0.100) 40 Example 213 48 5.30 6.20(0.134, 0.101) 40 Example 214 50 4.45 7.03 (0.134, 0.100) 33 Example 21551 5.44 6.14 (0.134, 0.102) 35 Example 216 52 5.50 6.00 (0.134, 0.102)31 Example 217 75 5.40 6.21 (0.134, 0.101) 36 Example 218 85 5.48 6.22(0.134, 0.101) 38 Example 219 86 5.44 6.25 (0.134, 0.102) 40 Example 22094 5.50 6.32 (0.134, 0.101) 33 Example 221 95 5.44 6.44 (0.134, 0.102)32 Example 222 96 5.34 6.38 (0.134, 0.101) 31 Example 223 97 5.38 6.20(0.134, 0.103) 35 Example 224 98 5.30 6.42 (0.134, 0.102) 34 Example 225100 5.35 6.30 (0.134, 0.101) 33 Example 226 102 5.44 6.22 (0.134, 0.102)30 Example 227 149 5.32 5.95 (0.134, 0.101) 29 Example 228 150 5.40 6.13(0.134, 0.101) 31 Example 229 151 5.44 5.89 (0.134, 0.100) 32 Example230 153 5.39 6.01 (0.134, 0.101) 29 Example 231 163 4.56 6.88 (0.134,0.100) 41 Example 232 173 4.51 6.93 (0.134, 0.100) 40 Example 233 1834.41 6.95 (0.134, 0.100) 39 Example 234 192 4.98 6.22 (0.134, 0.100) 40Example 235 193 5.02 6.34 (0.134, 0.101) 39 Example 236 194 4.72 6.53(0.134, 0.102) 66 Example 237 195 5.05 6.14 (0.134, 0.101) 40 Example238 196 5.25 6.22 (0.134, 0.100) 41 Example 239 198 5.59 6.19 (0.134,0.102) 32 Example 240 199 5.42 6.26 (0.134, 0.101) 32 Example 241 2005.11 6.11 (0.134, 0.100) 40 Example 242 242 5.35 6.22 (0.134, 0.102) 38Example 243 243 5.34 6.20 (0.134, 0.103) 37 Example 244 244 5.20 6.19(0.134, 0.100) 37 Example 245 245 5.22 6.05 (0.134, 0.103) 39 Example246 246 5.19 6.28 (0.134, 0.102) 40 Example 247 248 5.33 6.01 (0.134,0.100) 39 Example 248 249 5.10 6.21 (0.134, 0.101) 40 Example 249 2505.40 6.05 (0.134, 0.101) 33 Example 250 253 5.33 6.11 (0.134, 0.100) 33Example 251 263 5.31 6.21 (0.134, 0.103) 39 Example 252 273 5.36 6.08(0.134, 0.101) 32 Example 253 292 5.30 5.98 (0.134, 0.104) 30 Example254 293 5.30 5.80 (0.134, 0.100) 35 Example 255 294 5.11 6.22 (0.134,0.103) 36 Example 256 295 5.11 6.20 (0.134, 0.100) 40 Example 257 2965.24 6.10 (0.134, 0.102) 38 Example 258 298 5.41 6.21 (0.134, 0.100) 39Example 259 299 5.33 6.19 (0.134, 0.101) 30 Example 260 300 5.37 6.05(0.134, 0.100) 28 Example 261 301 5.18 6.03 (0.134, 0.101) 30 Example262 303 5.27 5.98 (0.134, 0.100) 33 Example 263 313 5.39 6.05 (0.134,0.101) 40 Example 264 323 5.05 6.23 (0.134, 0.101) 41 Example 265 3335.18 6.20 (0.134, 0.100) 30 Example 266 342 5.43 6.17 (0.134, 0.102) 34Example 267 343 5.40 6.21 (0.134, 0.103) 39 Example 268 344 5.34 6.38(0.134, 0.100) 38 Example 269 345 5.27 6.40 (0.134, 0.102) 41 Example270 346 5.15 6.10 (0.134, 0.103) 39 Example 271 348 5.20 6.15 (0.134,0.101) 40 Example 272 399 5.22 6.12 (0.134, 0.101) 33 Example 273 4005.05 6.20 (0.134, 0.102) 37 Example 274 401 5.11 6.14 (0.134, 0.102) 38Example 275 403 5.22 6.22 (0.134, 0.103) 36 Example 276 413 5.07 6.24(0.134, 0.100) 33 Example 277 423 5.05 6.31 (0.134, 0.100) 31 Example278 442 5.09 6.22 (0.134, 0.101) 32 Example 279 443 5.11 6.05 (0.134,0.103) 35 Example 280 444 5.21 6.09 (0.134, 0.101) 33 Example 281 4455.32 6.12 (0.134, 0.102) 31 Example 282 446 5.33 6.20 (0.134, 0.101) 28Example 283 448 5.34 6.25 (0.134, 0.102) 29 Example 284 449 5.43 6.17(0.134, 0.102) 30 Example 285 450 5.29 6.18 (0.134, 0.101) 35 Example286 451 5.40 6.20 (0.134, 0.103) 33 Example 287 453 5.38 6.11 (0.134,0.103) 34 Example 288 463 5.35 6.01 (0.134, 0.102) 33 Example 289 4735.37 6.05 (0.134, 0.101) 31 Example 290 484 5.40 5.99 (0.134, 0.102) 37Example 291 492 5.51 5.90 (0.134, 0.103) 38 Example 292 493 5.54 6.22(0.134, 0.102) 33 Example 293 494 5.34 6.19 (0.134, 0.104) 30 Example294 495 5.38 5.92 (0.134, 0.104) 28 Example 295 496 5.27 6.11 (0.134,0.101) 38 Example 296 498 5.25 6.02 (0.134, 0.102) 34 Example 297 4995.44 6.00 (0.134, 0.102) 32 Example 298 500 5.43 6.19 (0.134, 0.101) 31Example 299 555 5.48 6.35 (0.134, 0.101) 30 Example 300 556 5.55 6.09(0.134, 0.100) 40 Comparative E1 5.56 5.91 (0.134, 0.100) 28 Example 3-1Comparative BBQB 5.50 6.10 (0.134, 0.101) 30 Example 3-2 ComparativeTBQB 5.51 6.15 (0.134, 0.102) 29 Example 3-3

As shown from the results of Table 8, the organic light emitting devicesusing the electron transfer layer material of the blue organic lightemitting device of the present disclosure had a low driving voltage andsignificantly improved light emission efficiency and lifespan comparedto Comparative Example 3. Particularly, it was identified that Compounds5, 15, 25, 46, 50, 153, 163, 173, 194 and 198 were significantlyexcellent in all of driving, efficiency and lifespan.

The presumed reason for such results is that, when the invented compoundhaving proper length, strength and flat property is used as an electrontransfer layer, a compound in an excited state is produced by receivingelectrons under a specific condition, and particularly, when the excitedstate is formed in the heteroskeleton site of the compound, excitedenergy moves to a stable state before the excited heteroskeleton sitegoes through a different reaction, and the relatively stabilizedcompound is capable of efficiently transferring electrons withoutcompound decomposition or destruction. As a reference, it is consideredthat those having a stable state when excited are aryl or acene seriescompounds or multicyclic hetero-compounds. Accordingly, it is consideredthat the compound of the present disclosure enhances electron-transportproperties or improved stability resulting in excellency in all ofdriving, efficiency and lifespan.

The invention claimed is:
 1. A hetero-cyclic compound represented by thefollowing Chemical Formula] 2 or 3:

wherein, in Chemical Formula 2 and 3, at least one of R1 to R5 isrepresented by -(L2)p-(Z2)q and the rest are hydrogen; or deuterium, atleast one of R12 to R16 is represented by -(L3)r-(Z3)s, and the rest arehydrogen; or deuterium, L2 and L3 are the same as or different from eachother, and each independently a direct bond; or a substituted orunsubstituted C₆ to C₆₀ arylene group, Z2 and Z3 are the same as ordifferent from each other, and each independently selected from thegroup consisting of a substituted or unsubstituted pyridine group; asubstituted or unsubstituted pyrimidine group; a substituted orunsubstituted triazine group; a substituted or unsubstitutedphenanthroline group; a substituted or unsubstituted quinoline group; asubstituted or unsubstituted carbazole group; a substituted orunsubstituted dibenzofuran group; a substituted or unsubstituteddibenzothiophene group; a substituted or unsubstituted anthracene group;a substituted or unsubstituted phenanthrene group; a substituted orunsubstituted biphenyl group; a substituted or unsubstituted naphthylgroup; and —P(═O)RR′, p and r are an integer of 0 to 4; q and s are aninteger of 1 to 4; R6 to R11 are hydrogen or deuterium; and R, and R′are the same as or different from each other, and each independentlyhydrogen; deuterium; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₃ to C₆₀ cycloalkyl group; asubstituted or unsubstituted C₆ to C₆₀ aryl group; or a substituted orunsubstituted C₂ to C₆₀ heteroaryl group.
 2. The hetero-cyclic compoundof claim 1, wherein Chemical Formula 2 or 3 is represented by any one ofthe following compounds:


3. An organic light emitting device comprising: an anode; a cathode; andone or more organic material layers provided between the anode and thecathode, wherein one or more layers of the organic material layerscomprise the hetero-cyclic compound of claim
 1. 4. The organic lightemitting device of claim 3, wherein the organic material layer comprisesat least one of a hole blocking layer, an electron injection layer andan electron transfer layer, and at least one of the hole blocking layer,the electron injection layer and the electron transfer layer comprisesthe hetero-cyclic compound.
 5. The organic light emitting device ofclaim 3, wherein the organic material layer comprises a light emittinglayer, and the light emitting layer comprises the hetero-cycliccompound.
 6. The organic light emitting device of claim 3, wherein theorganic material layer comprises one or more of a hole injection layer,a hole transfer layer, and a layer carrying out hole injection and holetransfer at the same time, and one of the above-mentioned layerscomprises the hetero-cyclic compound.
 7. The organic light emittingdevice of claim 3, wherein the organic material layer comprises a chargegeneration layer, and the charge generation layer comprises thehetero-cyclic compound.
 8. The organic light emitting device of claim 3,comprising: an anode; a first stack provided on the anode and comprisinga first light emitting layer; a charge generation layer provided on thefirst stack; a second stack provided on the charge generation layer andcomprising a second light emitting layer; and a cathode provided on thesecond stack.